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The determination of the crystal structure of acetyltriphenylgermane by x-ray diffraction Harrison, Roy William 1967

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THE DETERMINATION OF THE CRYSTAL STRUCTURE OF ACETYLTRIPHENYLGERMANE BY X-RAY DIFFRACTION by ROY WILLIAM HARRISON B.Sc., University of B r i t i s h Columbia, 1965 A THESIS SUBMITTED IN PARTIAL FULFILMENT OF THE REQUIREMENTS FOR THE DEGREE OF MASTER OF SCIENCE i n the Department of Chemistry We accept t h i s thesis as conforming to the required standard. THE UNIVERSITY OF BRITISH COLUMBIA . July, 1967 In p r e s e n t i n g t h i s t h e s i s i n p a r t i a l f u l f i l m e n t o f the r e q u i r e m e n t s f o r an advanced deg ree a t the U n i v e r s i t y o f B r i t i s h C o l u m b i a , I ag r ee t h a t the L i b r a r y s h a l l make i t f r e e l y a v a i l a b l e f o r r e f e r e n c e and s t u d y . I f u r t h e r ag r ee t h a t p e r m i s s i o n f o r e x t e n s i v e c o p y i n g o f t h i s t h e s i s f o r s c h o l a r l y p u r p o s e s may be g r a n t e d by the Head o f my Depa r tmen t o r by h i s r e p r e s e n t a t i v e s . I t i s u n d e r s t o o d t h a t c o p y i n g o r p u b l i c a t i o n o f t h i s t h e s i s f o r f i n a n c i a l g a i n s h a l l no t be a l l o w e d w i t h o u t my w r i t t e n p e r m i s s i o n , Depa r tment The U n i v e r s i t y o f B r i t i s h C o l u m b i a V a n c o u v e r 8, Canada - 11 - ABSTRACT ' Acetyltriphenylgermane, (C^H^J^GeCOCH^, c r y s t a l l i z e s i n the monoclinic system with a = 15.30s b = 14»53j» c. = 7.6S A, and ^» 94.3 . The space group i s and there are four molecules per unit c e l l , thus each molecule forms an asymmetric unit i n the c e l l . The i n t e n s i t i e s of 2537 r e f l e c t i o n s were measured by means of a s c i n t i l l a t i o n counter using CuKcc ra d i a t i o n . The structure was determined by heavy atom Patterson and Fourier synthesis and refinement was by least-squares methods. The f i n a l discrepancy, R, f o r 1334 observed r e f l e c t i o n s i s 0.075. The compound was found to be tetrahedral about the germanium atom, with only small deviations caused by the spreading of the phenyl rings. The phenyl rings are planar with a mean C-C bond distance of 1.3#3 A, mean C-C-C bond angle of 120.0°, and a mean C-H bond distance of 1.09^  A. Interraolecular i n t e r a c t i o n causes one ring to deviate from a symmetric propeller orientation. Two Ge-C bond distances were found: Ge~Cphenyl distance o o of 1.945 A and G e - C a c e t y l distance of 2.011 A. The longer Ge-C bond i s attributed to contribution from a resonance structure i n which there i s no formal bond between germanium and the carbonyl carbon, r e s u l t i n g i n a p a r t i a l negative charge.on the oxygen and a p a r t i a l p o s i t i v e charge on the germanium. This i s supported by the electronegativity difference between carbon and germanium. The C=0 bond distance i s 1.20 AQ - i i i - TABLE OF CONTENTS PAGE T I T L E PAGE . . . . . . . . . . . . . . . . . . i ABSTiriACT o o o * * o « « * o * o « o o • * • « « « • « "XI. TABLE OF CONTENTS . . . . . . . i i i L I S T OF TABLES i v L I S T OF F IGURES . . i . . v ACKNOWLEDGEMENTS . . . • • • • v i INTRODUCTION . . . . . . . . . . . . . . 1 EXPERIMENTAL 4 STRUCTURE ANALYS I S 5 COORDINATES AND MOLECULAR DIMENSIONS . 9 DISCUSSION 16 BIBLIOGRAPHY 1 20 APPENDIX I. TABLE OF OBSERVED AND CALCULATED STRUCTURE FACTORS . . . . . . . 21 _ i v - LIST OF TABLES TABLE PAGE I- F i n a l p o s i t i o n a l parameters and standard deviations . . . . . . 10 II * F i n a l thermal parameters and standard deviatxons . . . . . . . . . . . . . . . . . 11 I I I . Equations of mean planes and angles between IV. Bond distances and angles with standard deviations . . . . . . . . . . 13 V 0 Shorter intermolecular distances . . . . . . 14 VI. Comparison of carbonyl stretching frequencies and electronegativity of o c-substituent . . . IS VII. Observed and calculated structure factors . 2J. - v - LIST OF FIGURES FIGURE PAGE 1. Perturbation of the energy l e v e l s of carbonyl by s i l i c o n . . . . . . . . . . . . 2 2. (a) Projected electron-density d i s t r i b u t i o n . . S (b) Perspective drawing showing atom numbering , $ 3. Molecular packing diagram 15 ~ v i - ACKNOWLEDGMENTS. I would l i k e to express my appreciation f o r the guidance and encouragement given to me by Dr. J, Trotter during the progress of t h i s work. I am also indebted to Dr. K. Yates f o r the c r y s t a l samples of the <*.-silyl and oc-germyl ketones-which he has provided* / / - 1 - INTRODUCTION . I n v e s t i g a t i o n s of the s p e c t r a l a c t i v i t y of the s i l y l and oC-germyl ketones (1-4) have shovm these compounds to d i f f e r markedly from t h e i r carbon analogues. The u l t r a v i o l e t spectra of b e n z o y l s i l a n e s are c h a r a c t e r i z e d by absorption at about 403-417 iy-, a s c r i b e d to a n-fi t r a n s i t i o n of the carbonyl group, i n v o l v i n g i n t e r a c t i o n w i t h the 3 d - o r b i t a l s of the s i l i c o n atom. A c e t y l s i l a n e s have absorption about 360-370 m^ w h i l e carbon analogues absorb at $0-100 m/i- shorter wavelength than the corresponding s i l i c o n compound. At the same time, the i n f r a r e d carbonyl s t r e t c h i n g v i b r a t i o n i s at a very low frequency: 1613 cm"-'- (6.1S/4 f o r benzoyl- and 1645 cm~l (6.OS//) f o r a c e t y l s i l a n e s , w h i l e the carbon analogues absorb at about 1636 cm"! (5.93/^) and 1715 cm-1 (5.33/4 r e s p e c t i v e l y . For o<.-germyl ketones, the s h i f t i n frequency i s o n l y s l i g h t l y lower. The positions of these absorption bands are r e l a t i v e l y i n s e n s i t i v e to the groups attached to s i l i c o n o r germanium. The f i r s t attempt to e x p l a i n the abnormal s p e c t r a l character of the o L - s i l y l and ©c-germyl ketones was made by Brook et a l (2) who a t t r i b u t e d the l a r g e i n f r a r e d s h i f t i n - c x - s i l y l ketones to the i n t e r a c t i o n between lone p a i r e l e c t r o n s on the carbonyl oxygen and vacant 3 d - o r b i t a l s on the s i l i c o n (^-tr bonding). This diT-ptr bonding would d i s t o r t and s t r e t c h the carbonyl group by t r a n s f e r of e l e c t r o n d e n s i t y toxrards the s i l i c o n atom, r e s u l t i n g i n a lowered fo r c e constant and thus a s h i f t i n the carbonyl s t r e t c h i n g v i b r a t i o n t o longer - 2 - wavelengths. West and Harnish (5) s i m i l a r l y interpreted the u l t r a  v i o l e t absortion spectra, using d-orbitals on the s i l i c o n , but i n terms of resonance interaction between the si l i c o n , atom and the lY-orbitals of the carbonyl group,pas shown i n f ' i g . l . 0 = C 0=C-SL TT /l V 7 -ML F i g . 1. Perturbation of the energy l e v e l s of. carbonyl by s i l i c o n , t r a n s i t i o n (n-ff ) results from t r a n s i t i o n s^if-p^ — S Q T P P 0 T T * where Tr*" i s the antibonding 1Y l e v e l . More recently, Brook, Kiv i s i k k , and LeGrow ( 6 ) , studying the spectral properties of p-substituted benzoyl- triphenylsilanes, concluded that the low infrared carbonyl stretching freo.uency i n benzoylsilanes was a result- of si g n i f i c a n t single-bond character i n the carbonyl group caused by the inductive release of electrons by. the adjacent s i l i c o n atom. In support of t h i s , Yates and Agollni (4) showed, the order of base strength to be I^SiCOPh£ R^GeCOFh > R^CCOPh, and Brook and Pierce.(7) shov:ed. that but not K'-silyl ketones absorb at lower frequency than t h e i r carbon - 3 - analogues. Thus, i n the ground state, o c - s i l y l and .<*-germyl ketones must have a s i g n i f i c a n t negative charge associated with the carbonyl oxygen atom, which i s consistent with contribution from a structure of the type + / 0 R 3 X - C ^ X P h To our knowledge, no crystallographic studies had been done on compounds of t h i s type, and a l i t e r a t u r e survey produced no X-C or C=0 bond lengths f o r them. It was f e l t that, i n 'such an investigation, i f accurate, bond lengths could be obtained, evidence for or against p a r t i c i p a t i o n of the d-orbitals of the s i l i c o n or germanium i n the bonding would be found i n a study of the bond lengths. The compound chosen was.acetyltriphenylgermane, which has a carbonyl stretching frequency at 1669 cm"-'- and peaks at 352, 365, and 3^0 m/t i n the u l t r a v i o l e t spectrum (3). 0 -. 4 - ,EXPERIMENTAL . ' • C r y s t a l s of a'cetyltriphenylgermane are white needles elongated along c.. The den s i t y was measured by f l o a t a t i o n i n aqueous potassium'iodide and th e u n i t c e l l dimensions and space group were determined from r o t a t i o n , Weissenberg, and precession f i l m s , and. on the G. E. Spectrogoniometer. C r y s t a l Data (-AjCuK*. = 1.5413 A; X,M0K*. = 0.7107 A) Acetyltriphenylgermane, (C5H5 J^GeCOCH-j; mol. wt-. 346.9, ra. pt. 121.5 - 123.0°. M o n o c l i n i c , a = 15.30±0.02, b - 14.53^0.02, c - 7.68± 0.02, f = 9 4 . S ± 0.3°. Volume of u n i t c e l l = 1704 P . D x (Z = 4) = I.35 g. cm.-3. . D m = 1.36 g. cm.~3. Absorption c o e f f i c i e n t f o r CuK^ X-rays, A= 1.541$ A, /"-s 26.4 cm.-1.• Absorption c o e f f i c i e n t f o r MoK^X-rays, ?V- 0.7107 A, y U = 19.0 cm."1, .Absent r e f l e c t i o n s : h0^ when-t i s odd OkO when k i s odd. Space group: P2^/c ( C ^ ) . T o t a l number of e l e c t r o n s per u n i t c e l l : F(000) = 712. The i n t e n s i t i e s of the r e f l e c t i o n s were measured on a General E l e c t r i c Spectrogoniometer, w i t h Single C r y s t a l Q r i e n t e r , s c i n t i l l a t i o n counter, approximately monochromatic CuK^ r a d i a t i o n being obtained by use of a n i c k e l f i l t e r and pulse height analyzer. A l l 2537 r e f l e c t i o n s i n the range 0< 29-^120° (corresponding to a minimum interplanar 0 spacing d =. 0 ,89.A) were examined, and 1^34 (72%) had an i n t e n s i t y above background. The 703 unobserved r e f l e c t i o n s were included i n the l a t t e r stages of the structure analysis with • |FQI = V 0 . 4 Zthreshold* i n t e n s i t i e s were corrected for background (approximately a function of 9 only). The c r y s t a l used f o r recording the i n t e n s i t i e s had dimensions 0.2 x 0.25 x 0 . 4 mm and-was mounted with c* p a r a l l e l to the. <f> axis of the goniostat. No absorption corrections were applied. Lorentz and pol a r i z a t i o n corrections were applied and structure amplitudes derived. - STRUCTURE ANALYSIS The position of the germanium atom was determined from a three-dimensional Patterson synthesis as (0.7375, 0.5271, 0 . 3 1 4 6 ) . Structure factors were calculated f o r a l l the r e f l e c t i o n s using the scattering factors f o r Ge (corrected f o r anomalous dispersion) from the International Tables (9) and a temperature factor, B, of 3-0 A^ ?(R = 0 . 3 4 ) . A three- dimensional Fourier series was summed with the signs of the structure amplitudes based on the germanium atom contribution. Peaks corresponding to a l l of the atoms (except hydrogens) appeared on the electron density map. The oxygen atom was distinguishable from the methyl carbon by both peak height and. bond distance. The structure "factors for a l l 22 atoms were calculated (R = 0 . 2 4 ) , setting - 6 - B = 3,0 for a l l atoms and using the C and 0 scattering factors from the International Tables ( 9 ) , The positional and i s o t r o p i c thermal parameters and an o v e r a l l scale f a c t o r were refined by block diagonal least-squares methods. The function minimized was £,w(F 0_F c) 2, withVw~=.0 f o r unobserved r e f l e c t i o n s , Vw - 1 when I F Q I ^ 1 5 , and Vw" = 15/ Zo when |Fj0|>15o Several cycles of least-squares refinement reduced R to 0.0#7. A comparison of the calculated and observed structure factors showed twenty-five r e f l e c t i o n s , including the following strong " '•. refle c t i o n s ' (311, 402, 212), had serious disagreement',. Of these, eleven were corrected by comparison with films and the rest, a l l very weak r e f l e c t i o n s , were removed from the least-squares refinement. Following several more l e a s t - squares cycles, a ( F Q - Z C ^ difference synthesis was computed to locate the hydrogen atoms. A l l f i f t e e n phenyl hydrogens were located, but one of these, H{26), gave a C-H bond o distance of 0.67 A and so was placed at i t s t h e o r e t i c a l position. Attempts to locate the methyl hydrogens were unsuccessful. Further refinement, including the hydrogen-, atoms at fixed positions and with B = 6*5 A , reduced R to 0.073. At t h i s stage, an analysis of the values of (Fo-F c) suggested a more appropriate weighting scheme: V"w" - ; 1 , The unobserved r e f l e c t i o n s were also included,v.with - 7 - ' IFQI = V0.4 ^threshold and were given a weight V™-*3 0.62. The average w(F 0-F c) was novr approximately constant over a l l values of F Q taken at i n t e r v a l s of 5. Refining all°-37. atoms with the new weighting scheme changed R to 0.077. Ge, 0, C (3 ) , 0(4), C(5), C ( l l ) , and C(l7) were then refined f o r three cycles with anisotropic temperature factors, the hydrogens being fixed i n t h e i r best position (peak position or f i r s t or second refinement position) according to bond length a f t e r the f i r s t cycle, and the remaining carbon atoms being fi x e d i n position after the second cycle, reducing R to 0.073. A f i n a l structure factor calculation, including the 14 r e f l e c t i o n s that were removed from the refinement, gave R - 0.075. The f i n a l measured and calculated structure factors are l i s t e d i n Table VI.(Appendix I ) . A f i n a l three- dimensional Fourier series was summed and superimposed sections of the re s u l t i n g electron-density d i s t r i b u t i o n are shown i n Figure 2, together with a drawing of the structure giving the atom numbering used i n the analysis. A f i n a l o difference map showed maximum fluctuations bf ± 0.5eA">. (a-) Electron-density projection along the c axis. Contours are at intervals of 1 e. sta r t i n g at 2' e. A"*^  for carbon, and of 10 e. A-3 s t a r t i n g a t f o r Ge. 10 e. (b) Perspective drawing o f the structure giving, the numbering used, - 9 - COORDINATES AND MOLECULAR DIMENSIONS The f i n a l p o s i t i o n a l p a r a m e t e r s and t h e i r s t a n d a r d d e v i a t i o n s a r e g i v e n i n T a b l e I. x , Z> a n d z. a r e f r a c t i o n a l c o o r d i n a t e s r e f e r r e d t o t h e m o n o c l i n i c c r y s t a l a x e s ; c r ( x ) , c r ( y ) , a n d c r ( z ) a r e t h e s t a n d a r d d e v i a t i o n s o f t h e o c o o r d i n a t e s ( i n A) c o m p u t e d f r o m t h e l e a s t - s q u a r e s r e s i d u a l s . The p o s i t i o n s o f t h e h y d r o g e n a toms a r e l e a s t a c c u r a t e l y d e t e r m i n e d and a r e n o t c o n s i d e r e d f u r t h e r . T a b l e I I g i v e s t h e f i n a l t h e r m a l p a r a m e t e r s , where Uj.j a r e t h e c o m p o n e n t s o f t h e v i b r a t i o n t e n s o r s , w r i t t e n i n m a t r i x f o r m , and r e f e r r e d t o t h e a x e s a * , b * , and c * . The e q u a t i o n s o f t h e mean p l a n e s o f t h e t h r e e p h e n y l r i n g s a r e g i v e n i n T a b l e I I I , a l o n g w i t h t h e p l a n e s t h r o u g h C(3 ) - G e - C ( p h e n y l ) and t h e i n t e r p l a n a r a n g l e s . Bond d i s t a n c e s and v a l e n c y a n g l e s t o g e t h e r w i t h t h e i r s t a n d a r d d e v i a t i o n s a r e l i s t e d i n T a b l e - I V , and T a b l e V l i s t s a l l t h e c r y s t a l l o g r a p h i c a l l y o i n d e p e n d e n t i n t e r m o l e c u l a r d i s t a n c e s s h o r t e r t h a n 3.8 A . Two i m p o r t a n t d i s t a n c e s i n v o l v i n g t h e C ( l l ) - C ( l 6 ) r i n g s a r e a l s o l i s t e d . F i g u r e 3 i l l u s t r a t e s . t h e p a c k i n g o f t h e m o l e c u l e s . - 10 - Table I Final positional parameters (fractional) And standard deviations (A). Atom X Z z <r (x) <r<z) •'Ge(l) 0.7354 . 0.5264 O.3163 0.0015 0.0015 0.0015 0(2) 0.6499 0.6951 0.2546 0.011 0.012 0.012 C(3) 0.6615 0.6227 0.1862 0.014 0.015 0.015 CH3U) 0.6200 0.6011 0.0052 0.023 0.023 0.021 C(5) 0.3176 0.5900 O.L8O6 0.013 0.013 0.013 6 0.9082 0.5855 0.4723 0.015 0.016 0.015 7 0.9629 0.6324 0.5891 0.017 0.019 0.018 8 0.9307 0.6352 0.7191 0.018 0.020 0.019 9 0.3419 .0.6933 0.7263 0.016 0.017 0.016 10 0.7854 0.6451 0.6095 0.016 0.017 0.017 11 0.6534 0.4484 0.4411 0.015 0.014 0.014 12 0.5776 0.4199 • 0.3651 0.019 0.020 0.019 13 0.5260 O.36OO 0.4554 0.021 0.022 0.021 14 0.5520 0.3306 0.6203 0.019 0.020 0.020 1 15 0.6315 0.3596 0.6976 0.021 0.022 . 0.021 16 0.6345 0.4177 0.6072 0.018 0.019 0.013 17 0.7961 0.4539 0.1501 0.015 01014 '• 0.014 18 0.7367 0.3602 O.1383 0.017 :'' 0.018 0.017 19 0.8311 O.3108 O.OI83 0.020 0.021 0.020 20 0.8855 0.3539 -0.0353 0.020 0.021 0.020 21 0.8959 0.4478 -0.0778 0.020 .0.020 • 0.020 22 0.3508 . 0.4933 0.0384 0.017 0.017 0.017 H(23) 0.942 0.533 . 0.392 24 1.034 0.617 0.595 25 0.974 0.720 0.316 26 0.816 0.733 0.828 27 - 0.724 0.652 0.626 . 23 0.553 0.444 0.225 29 O.467 0.354 0.417 cr(x) = cr(z) = o-(z) = 0 30 0.502 0.277 0.699 31 0.649 0.335 0.857 32 0.742 0.446 • 0.683 33 0.775 0.317 0.250 , 34 0.825 0.242 0.011 35 0.392 0.300 -O.I83 36 0.940 0.435 -0.148 37 0.850 0.575 0.042 - 11 - Table II F i n a l thermal paramo deviations ( H i j i n 1 ;ers and standard ' x 102; B i n ! 2 ) , Atom Ge(l) 0(2) C(3) CHo(4) C(5) C.(ll) C(17) Mean B H i i H l 2 Ul3 u 2 2 H23 . H33 <r(U) 3.54 4.57 -0.19 0.15 4.29 -0.10 4.55 0.07 5.33 5.31 0.74 -1.37 6.21 -0.53 3.14 0.60 4.15 4.27 0.14 0.54 5.45 0.66 6.32 .0.71 7.26 10.45 2.03 -2.77 9.33 0.69 7.41 1.19 3.46 4.36 -0.39 0.31 3.45 0.21 4.74 0.61 3.93 5.51 -0.41 0.43 4.71 -0.72 4.74 0.67 3.73 5.25 -0.31 -0.23 5.02 -0.36 4.31 0.66 Atom B o~(B) . C(6) 4.24 0.23 7 5.33 0.35 3 5.61 0.37 9 4.30 0.31 10 4.59 0.30 12 5.73 0.37 13 6.52 0.43 . 14 5.91 0.39 15 6.47 0.42 16 5.27 0.35 13 4.96 0.32 19 6.23 0.41 20 6.36 0.42 21 6.00 0.40 22 4.61 0.31 - 12 - Table III Equations of mean planes and angles between planes. Equations of mean planes, in the form iZJ + rnY_' t 0^' + P. = 0, where X' , Y ' , Zf are coordinates in A referred to orthogonal axes a., b, c, *. Maximum Plane Atoms 1 m n R Displacement 1 1,5-10 -0.022 -0.783 0.615 4.779 0.016 2 1,11-16 0.465 -0.799 -0.330 1.913 0.021 3 .1,17-22 -0.716 0.117 -0.639 3.663 0.016 4 1,3,5 -0.720 -0.045 0.693 6.620 0.0 5 1,3,11 -0.056 -0.606 -0.793 7.175 0.0 .6 1,3,17 -0.764 -0.633 -0.094 13.550 0.0 Angles between planes. i / Planes Angle 1 - 4 61.5° 2 - 5 40.6' 3 - 6 57.5 4 - 5 11$.3° 4 - 6 120.9 5 - 6. 120.3 - 13 - Table IV Bond distances (A) and angles (degrees) with, standard deviations. Germanium-Carbon bond lengths Ge-C(3) cr 2.011 0.015 Ge-C(5) Ge-C(ll) Ge-G(l7) 1.940 0.014 1.945 0.014 1.950 0.014 mean Ge-Cp^enyl 1.945 ± 0.008 A C(3)-Ge-C(5) C(3)-Ge-C(ll) C(3)-Ge-C(l7) C(5)-Ge-C(ll) C(5)-Ge-C(l7) C(ll)-Ge-C<17) 107.4° 0.6 103.2 0.6 109.2 0.6 110.1 0.6 111.4 0.6 110.5 0.6 Phenyl r i n ^ s C(5) - c ( 6 ) 1.40 G(6) - C(7) 1.36. C(7) - c(3) 1.38 c(3) - C(9) 1.37 C(9) -•C(10) 1.39 C(10) - c(5) 1.40 C ( l l ) - C(12) 1.39 C(12) - C(13) 1.40 C(13) - C(14) 1.37 C(14) - C(15) 1.37 C(15) - C(16) 1.40 C(16) - C U D 1.38 C(17) - C ( l 8 ) 1.37 c U 3 ) - C(l9) 1.39 C(19) - C(20) 1.35 C(20) - C(21) 1.38 C(21) - C(22) 1.38 C(22) - C(17) 1.41 mean C a r . - c a r . 1.38 3 C(10)-C(5)-C(6) C(5)-C(6)-C(7) C(6)-C(7)-C(S) C(7)-C(8)-C(9) C(8)-C(9)-C(10) C(9)-C(10)-C(5) C(16 C ( l l C(12 C(13 C(14 C(15 C(22 C(17 C(l3 C(19 C(20 C(21 - G ( l l ) . -C(12). -C(13)- -C(14)- -C(15). -CU6). -C(17). -C(18). -C(19)- -C(20). -C(21). -C(22). •C(12) •C(13) •C(14) .C(15) •C(16) •CUD •C(l8) •C(19) •C(20) .0(21) •C(22) •0(17) 118.1° 120.4 121.2 119.6 119.7 120.9 118.2 119.9 121.6 118.8 120.2 121.4 118.7 120.2 120.6 120.7 119.4 120.4 mean C-H 1.09 ± 0.06 \ 0(3) .- CH 3(4) 1.51± 0.03 A 0(3) - 0(2) . 1.20 ± 0.02 A - 14 - Table V Shorter Intermolecular Distances ( A l l c r y s t a l l o g r a p h i c a l l y independent distances < 3 .3 A . between molecule 1 at x, y_, .z, and neighbouring molecules are l i s t e d as well as two distances involving in t e r a c t i o n of C ( l l ) - C ( l 6 ) rings.) Atom (of molecule l ) 0(2) 0(2) 0(2) 0(2) C(21) 0(2) C (5) . C(6) C(3) C(6) C(13) C(12) to Atom of Molecule •# C(14) C(10) C(9) CHo(4) c(ii) C(13) C(9) C(6) C(14) C (7) C(14) C(13) 2 6 6 3 7 2 6 4 2 4 5 2' Distance U ) 3.33 3.36 3 .33 3 .53 3 .64 3.72 3.74 3.75 3.76 3 .73 3.32 3 .33 Molecule 1 at X y z 2 at 1-x ' 1--y l -z - - 3 at X Ih -y . i + z 4 at 2-- X 1--y 1 -z 5 at X 1 a -y + z 6 at X Ih -y - i + z 7 at 2-- X • 1--y -z - 15 - Figure 3. View of the structure along c., i l l u s t r a t i n g the packing of the molecules. Heavier l i n e d molecules are closer to the viewer. » 16 - DISCUSSION The analysis has shown acetyltriphenylgermane to be tetrahedral about the germanium atom corresponding to sp3 hybridization on the germanium, as was expected. Di s t o r t i o n from t h i s tetrahedral shape caused by the spreading of the phenyl rings i s very small, the average Cacetyl'^-^phenyl angle being 103,3°, and the average Cphenyl- G e- Cphenyl angle being 110.7°. The angles between the C(3), Ge, Cphenyl planes are 11$.$, 120.9, and 120.3°. The three phenyl rings, are planar (maximum deviation from ri n g plane i s 0.021 A) with a mean C-C bond distance of 1.3$3± 0.006 A and a mean C-C-C angle of 120.0 ±0.4°. The mean C-H bond distance i s 1.09 ±0.06 A. The rings are oriented i n a propeller fashion about germanium with angles between the ri n g planes and the C(3), Ge, Cp^enyl planes of 61.5, 40.6, and 57.5°. The smaller interplanar angle of the r i n g containing C ( l l ) - C ( l 6 ) appears to be caused by interraolecular i n t e r a c t i o n between t h i s r i n g and symmetry related C ( l l ) - C ( l 6 ) rings. Increasing t h i s angle to 60° would cause severe carbon-carbon interactions (shortening of the C(12)-C(13) and C(13)-C(14) intermolecular distances i n Table V). The germanium-carbon bonds are not a l l equivalent. The mean Ge-Cp^enyl bond distance i s 1.945 ±0,00$ A which agrees with the bond distance found i n CH^GeH^ by microwave spectroscopy of 1.9453± 0.0005 A (10). The G e - C a c e t y i bond length i s s i g n i f i c a n t l y (4c) longer at 2.011±0.015 A. A - 17 - bonding scheme responsible for the lengthening of t h i s Ge-C bond can be-deduced by comparing the resonance structures available to the germanium compound with those of the . corresponding carbon analogue. When the oc-substituent l b l i b I l l b IVb (underlined) i s carbon, Ia, the difference i n the electro n e g a t i v i t i e s of the carbon and oxygen i n the carbonyl group r e s u l t i n contribution from the resonance structure I l a . When the c c-substituent i s germanium,lb, the electronegativity difference i n the carbonyl group i s s t i l l present, and contribution from l i b would be expected. However, the <x.-gerraanium atom i s more electropositive than the carbonyl carbon and the positive charge i s more l i k e l y to reside on the germanium than on the carbon. Contribution from the re s u l t i n g resonance structure, I l l b , with no formal bond between the germanium and carbon atoms, explains the long Ge-C bond length. Further d i s s i p a t i o n of the positive charge to the ortho and para carbons of the phenyl rings i s also possible, IVb© I t i s not possible, '.however, to determine whether t h i s occurs, since the resultant shortening of the Ge-Cp nenyl bonds would be too small to be noticed 0 The f i n a l structure i s thus probably derived from l b with s i g n i f i c a n t - 13 - contribution from I l l b , . i e . , o*- i* I ^Ge—C—CH^ This explains the negative charge found on the carbonyl oxygen by Yates and Agolini (4) and gives a normal C=0 bond length (experimentally 1,20 ±0.02 A). No evidence f o r pa r t i c i p a t i o n of the germanium d-orbitals was foundo The r e s u l t s of the spectral studies on the o c - s i l y l and ot-germyl ketones (1-3) and the b a s i c i t y studies of Yates and Agolini (4) suggest that the amount of negative charge on the carbonyl oxygen increases i n the order C<Ge<Si, so that i f the inductive effect i s solely responsible f o r the charge d i s t r i b u t i o n , i t i s expected that the el e c t r o n e g a t i v i t i e s would be i n the reverse order, i e . , C>Ge>Si. The electro n e g a t i v i t i e s determined by A l l r e d and Rochow ( l l ) support t h i s as shown i n Table VI, i n which the trend i n the carbonyl Table VI „ Comparison of the carbonyl stretching c frequencies and the electronegativity of the oc-substituent. ; Compound C=0 stretching f r e q . (cm~l) Electronegativity 2.50 2.02 1.74 stretching frequency i s closely p a r a l l e l e d by that of the el e c t r o n e g a t i v i t i e s . While these el e c t r o n e g a t i v i t i e s are s t r i c t l y only those of the i s o l a t e d atom, since the environment of the oC-substituent i s i d e n t i c a l i n each compound t h e i r ^ 3CCOCH 3 1721 (2) ^3GeCOCH3 1669 (3) ^ 3Sicoce 3 1645 (2) - 19 - r e l a t i v e values should be correct.. These trends suggest that the S i - C a c e t y - ^ bond i n the analogous s i l i c o n compound should be r e l a t i v e l y longer than the corresponding bond i n the germanium compound and a structure analysis of acetyltriphenylsilane would be useful i n supporting the bonding scheme which has been proposed f o r the o<-germanium ketone* / - 20 - BIBLIOGRAPHY 1 0 A. G0 Brook, Am. Chem, Soc. 22,'. 4373 ( 1 9 5 7 ) . 2. A. G. Brook', M. A. Quigley, G0 J. D. Peddle, N. V a Schwartz., and C 0 M. Warner, J. Am. Chem. Soc. 82, 51.02 ( I 9 6 0 ) . • 3„ A. G. Brook and G. J„ D, Peddle, J. Organometalo!'.Chem0 2, 106 (1966). • 4 . K. Yates and F 0 A g o l i n i , Can. J. Chem. L 4 5 2229 (1966) 5o D. F. Harnish and R. West, Inorg. Chem. 2, 1082 (1963) ' 6 a A. G0 Brook, R. Kivi s i k k , and G. E„ LeGrow, Can. J. Chem. i i , 1175 (1965). 7. A. G. Brook and J. B 0 Pierce, Can. J . ' Chem. 4 2 , 293 (l964)o 3. G. J. Peddle, J. Organometal. Chem. 436 (1966). 9. International Tables f o r X-ray Crystallography, Vol. I l l Kynoch Press (1962). 10c V . W. Laurie, J . . Chem. Phys. 3 0 , . 1210 ( l 9 5 9 ) o 11. F. A. Cotton and G. Wilkinson, "Advanced Inorganic Chemistry", Wiley, New York (1962). - 21 - APPENDIX I Table VII" Observed and Calculated Structure Factors {* indicates a r e f l e c t i o n which was not included i n the least-squares refinement. Negative F Q values indicate an unobserved re f l e c t i o n . ) - 22 - Table VII 0 1 1 6 8 . 3 73.7 -14 7 11.4 -8.7 2 73.1 69.8 -J 15" 2 15.2 - 1 8 . 2 hk -I ! V 152.ft 1 71.9 -144.4 75.4 15 7 -15 7 -2.2 -2.7 4.7 0 . 3 'I \ 36. ft 31.C 36. 1 29.7 -4 IC 7 19. C 2 9.5 17.5 -12. t 1 Fo Z 1 1 2 7 . * 27.7 0 9 7.7 -6.2 - 3 2 25.8 -12.7 5 tC 2 -2 .7 -0.6 1 " l 1 1 AC.2 1 132.8 -AC.7 144.5 I 9 -I 9 7.1 26. 7 7.1 25.8 j 1 1 1 . ! 72.7 - l U . a - 7 1 . 3 -5 tC 6 IC 2 18.6 2 19.C 19.4 -2C.5 t c 0 2.1 1 A3.3 -59.7 2 9 - 1 . 9 C O 4 i . e -31. t -6 IC 2 14.4 13.7 X c 9 c c 0 143.4 5.5 -148.1 -10 .2 -1 ! I 7ft.8 1 T9 .4 70 . 3 75.9 -2 9 3 9 -1 .5 13.9 -2.7 -13.3 \ 73.4 44.8 7 3 . 3 BC.6 7 tC - 7 IC 2 -2.2 2 -2.2 1.7 9.2 4 0 c 7 .9 - A . 4 + 9 1 1 ae. e - 8 5 . T -3" 4 -4.1 -6 2 27.1 27. t B IC 2 - 7 . 2 1 .5 * c « c c c 22.e 26.7 -19.9 -24.5 ~l ! 1 38 .7 1 9.4 38.6 C.C • 4 « -4 9 -1.9 n.s 1.7 13.A -1.7 I 79.5 3.C -60.8 -8 IC 9 IC 2 7.5 7 - 2 . 7 -5.6 -3.2 1 t c 9.ft -T.4 1 40.3 -48. ft 9 9 -2 .C - 2 . 9 47.5 -44.8 -9 IC ? 14.2 - 1 5 . 3 a c « c a 0 24. 8 2C.5 24.A -19.4 -T 1 1 81.1 I 3ft.ft 11.7 -37.6 -5 9 6 9 -2 C -2.1 l .C - C Z I - 1 . 9 I - 1 . 5 -C .6 1 . 3 10 IC -10 IC 2 -2.5 2 1 C 5 3.C *.9 10 c c 45.C -45.4 9 1 1 16.3 -33 .1 -6 4 14.1 -lfc.2 -9 2 2 3 C 8 5 1 . 2 11 IC 2 -2 .4 -7.2 11 c 0 4 * .9 49 .A —8 1 1 24. C 24.C 7 9 -7.1 2.8 10 2 ! 17.« 34.2 -11 IC 2 11.4 1ft. 1 12 C a i f .e 21.3 . < 1 1 49.3 -45.2 - 7 9 -2.1 -4.2 - 10 2 I 2C.ft -20.0 12 tC 2 - 7 . 2 -1.5 13 t d 43.C -4C.4 1 17.9 11.C a 9 -2.2 1-3 2 ft.8 3.3 -12 IC 2 -2.1 -7.0 1* c IS C c c 9.2 2ft.1 -4 .7 24. 1 -10 1 1 19.2 1 48.2 U . 5 -46 . 1 ~ H 9 9 9 - 2 . 2 7.8 -2.2 -6 .0 " l 2 ] t 42.1 2 32.4 -42.9 -10.C -13 IC 0 17 2 -1.2 2 2*. 1 -4 .0 21. C 16 C IT C c 5^1 22.C - a . 5 -20.4 -11 1 1 92.5 I 9.9 46.5 -8.3 -•) 9 10 9 -2.2 11.1 1.9 10.8 "15 5 2 75.3 2 8.7 25.2 8.9 1 17 -1 12 2 IC.ft 2 - 2 . 2 8.7 -5.1 0 2 c 119.C 115.A 1? 1 1 23.3 -22.a -10 9 5.4 89 - 1 3 2 2 2 9 . 1 10.1 2 17 2 71.4 -70.5 t 2 4.2 2.C 1 92. C 51.2 U 5* - 2 . 2 .7 2 23.7 74.5 -2 17 2 8 . 4 -11.3 2 2 3 2 5 121.9 JC.4 -118.9 10.4 - 1 J 1 1 2C.7 I -2 .5 -JI.3 -4 .7 -11 « 12 9 7.9 -2.4 - 2 . 8 -2 .4 "!? I 7 8.9 2 11.5 -8.4 -t l.7 3 17 -3 12 2 11.7 2 -2.2 -9.4 6 . 3 4 Z 9 2 69 . 7 49.C 72.C . -46.5 - i l l 1 25.3 1 44.4 25.a -42.1 -12 4 13 9 -2.5 -2.3 -0.7 -3 .9 2 .14.5 2 14.5 -17.7 -15.7 4 12 -4 12 2 5.1 7 - 2 . 2 9.0 . - 7 . 2 A 2 c 79.2 -74.7 i s l I - 2 .5 5.6 -13 9 - 2 . 4 - 1 . 4 - 16 2 2 -2.3 6.4 5 12 2 - 2 . 2 3.7 7 2 4 9 . 9 « . « I I I . C 10.9 14 4 -2.1 -3.8 2 44.9 -49.5 - 5 . 1 2 2 5.9 -8 . I' 1 2 « 2 I 44. ft SC.9 43.4 -J3.1 -it ! 1 M . J 1 21.A -19 ,4 22.1 -14 9 0 11 -2.2 - 2 . 1 - 4 . 4 -0.2 .{ ; ? 75.9 i 74.8 -75.5 8C.9 6 12 -6 12 -2.22 12. ft -t5.5 13.5 1C 2 11 2 13.5 H . C -14.1 31.4 1 I - 2 . 2 1 9.5 -».i 2.a 1 11 -1 11 19.7 8.1 20.3 -6.1 .5 J 2 57.5 ? t.e 54.6 - 3.4 7 12 -7 12 2 -2.2 2 It.5 - 2 . 3 9.7 12 2 c 22. ! 18.1 t 3 1 1 U . 4 -113.3 2 11 -2.1 1.3 3 2 61.4 55.4 8 17 2 9.1 7.5 IS 2 1ft.4 -11.4 I 98.7 99.6 - 7 11 -2.1 -0 .8 2 59.1 -56.3 -8 12 -2 5 -2.9 14 2 c IC.4 -10.5 2 3 [ 96.A -93.7 3 It 21.4 -7^.5 4 2 83 .4 -77,5 9 12 2 -2.1 1 619 2 c 25.9 2 5 . 3 —2 1 1 19.3 -40.2 -3 11 7.5 7.4 . 4 2 71.9 -2 J.C -9 12 2 1C.7 -12.1 It 2 17 a I -2 .3 21.7 1.9 -2C. ) _\ \ 1 *0 .2 i e.9 82.9 - 3 . C 4 11 -4 11 -7.2 7.5 -3.7 -8.1 . * 7 J l . 12 6 7 . 3 -28.8 44.7 .10 12 - 10 12 2 5.7 2 -2.3 "8.6 3 . 3 0 * 47.2 -42.1 4 ) 1 A.C -6.9 9 11 5.8 8.5 6 2 3 C C 31.1 -11 12 2 12. t 11.1 2 * 2 4 . ; i t . 2 25.9 -B4.4 9 1 I 7.5 1 94 .7 4.8 -89.2 -3 11 6 11 ice 12.1 -11.5 -11.6 _ 7 2 42. C 2 -1 .8 4 4 . 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