Structural Study in Relation With Captodative Substituent Effect .4. X-ray Study of P,P'-substituted 2,3-dimethyl-2,3-diphenyl-1,4-butanedinitrile With Phenylogous Captodative Or Dicapto-substitution

Parfonry, A.;Tinant, Bernard;Declercq, Jean-Paul;Van Meerssche, M.;Viehe, HG.;et.al.
(1987) Societes Chimiques Belges. Bulletin — Vol. 96, n° 2, p. 89-95 (1987)

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  • Parfonry, A.
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  • Tinant, BernardUCLouvain
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  • Declercq, Jean-PaulUCLouvain
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  • Van Meerssche, M.autre
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  • Klein, JeanUCLouvain
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  • Viehe, HG.
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Abstract
In order to compare captodative (cd) and dicapto (cc) - substitution effects on molecular geometry, we have determined by X-ray diffractometry the structures of the four p, p′-substituted (methylthio, dimethylamino, methoxy-carbonyl and cyano) 2,3-dimethy 1-2, 3-diphenyl-1,4-butanedinitrile (2a-d). The meso isomers are found to be of centrosymmetric conformation and within experimental error the geometry of each of the four molecules is the same. No significant difference on the central C-C bond length is observed for phenylogous cd (2a, b) and cc (2c, d)-substitution. The mean value of the C-C central distance is 1.602 (2)Å and much longer than expected from force-field calculations.
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Parfonry, A., Tinant, B., Declercq, J.-P., Van Meerssche, M., Klein, J., Merenyi, R., & Viehe, HG. (1987). Structural Study in Relation With Captodative Substituent Effect .4. X-ray Study of P,P’-substituted 2,3-dimethyl-2,3-diphenyl-1,4-butanedinitrile With Phenylogous Captodative Or Dicapto-substitution. Societes Chimiques Belges. Bulletin, 96(2), 89-95. https://doi.org/10.1002/bscb.19870960202 (Original work published 1987)