Theory of Structural Isomerism. Vicinal vs. Geminal Homodisubstituted Molecules

N. D. Epiotis; J. R. Larson; R. L. Yates; W. R. Cherry; S. Shaik; F. Bernardi

doi:10.1021/ja00465a011

Theory of Structural Isomerism. Vicinal vs. Geminal Homodisubstituted Molecules

N. D. Epiotis, J. R. Larson, R. L. Yates, W. R. Cherry, S. Shaik, F. Bernardi

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Abstract

The linear combination of fragment configurations (LCFC) method is utilized to predict the most stable structural isomer of disubstituted alkanes and alkenes. It is argued that the 1,10 isomer (X₂A-A or X₂B⩵B) will be more stable than the 1,2 (cis or trans) isomer (XA-AX or XB⩵BX) when the two substituents are identical or electronically similar. Furthermore, a connection is made between the relative stability of the 1,1 and 1,2 isomers and A-A or B⩵B bond strengths in these two isomers. The predictions agree with known thermochemical data, microwave data, and quantum mechanical calculations.

Original language	English
Pages (from-to)	7460-7464
Number of pages	5
Journal	Journal of the American Chemical Society
Volume	99
Issue number	23
DOIs	https://doi.org/10.1021/ja00465a011
State	Published - 1977
Externally published	Yes

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title = "Theory of Structural Isomerism. Vicinal vs. Geminal Homodisubstituted Molecules",

abstract = "The linear combination of fragment configurations (LCFC) method is utilized to predict the most stable structural isomer of disubstituted alkanes and alkenes. It is argued that the 1,10 isomer (X2A-A or X2B⩵B) will be more stable than the 1,2 (cis or trans) isomer (XA-AX or XB⩵BX) when the two substituents are identical or electronically similar. Furthermore, a connection is made between the relative stability of the 1,1 and 1,2 isomers and A-A or B⩵B bond strengths in these two isomers. The predictions agree with known thermochemical data, microwave data, and quantum mechanical calculations.",

author = "Epiotis, {N. D.} and Larson, {J. R.} and Yates, {R. L.} and Cherry, {W. R.} and S. Shaik and F. Bernardi",

year = "1977",

doi = "10.1021/ja00465a011",

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T1 - Theory of Structural Isomerism. Vicinal vs. Geminal Homodisubstituted Molecules

AU - Epiotis, N. D.

AU - Larson, J. R.

AU - Yates, R. L.

AU - Cherry, W. R.

AU - Shaik, S.

AU - Bernardi, F.

PY - 1977

Y1 - 1977

N2 - The linear combination of fragment configurations (LCFC) method is utilized to predict the most stable structural isomer of disubstituted alkanes and alkenes. It is argued that the 1,10 isomer (X2A-A or X2B⩵B) will be more stable than the 1,2 (cis or trans) isomer (XA-AX or XB⩵BX) when the two substituents are identical or electronically similar. Furthermore, a connection is made between the relative stability of the 1,1 and 1,2 isomers and A-A or B⩵B bond strengths in these two isomers. The predictions agree with known thermochemical data, microwave data, and quantum mechanical calculations.

AB - The linear combination of fragment configurations (LCFC) method is utilized to predict the most stable structural isomer of disubstituted alkanes and alkenes. It is argued that the 1,10 isomer (X2A-A or X2B⩵B) will be more stable than the 1,2 (cis or trans) isomer (XA-AX or XB⩵BX) when the two substituents are identical or electronically similar. Furthermore, a connection is made between the relative stability of the 1,1 and 1,2 isomers and A-A or B⩵B bond strengths in these two isomers. The predictions agree with known thermochemical data, microwave data, and quantum mechanical calculations.

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Theory of Structural Isomerism. Vicinal vs. Geminal Homodisubstituted Molecules

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