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Ethyl anion preferred conformation
Author(s) -
Goodman Lionel,
Sauers Ronald R.
Publication year - 2004
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.20398
Subject(s) - conformational isomerism , chemistry , steric effects , natural bond orbital , ion , ab initio , proton , computational chemistry , quantum chemical , crystallography , molecule , density functional theory , stereochemistry , organic chemistry , physics , quantum mechanics
Ab initio architecture and torsional barrier for ethyl anion, C 2 H − 5are analyzed using natural bond orbital methodology. The B3LYP/6‐311++G(3 df ,2 p ) 2‐kcal/mol torsional barrier between the preferred staggered and higher‐energy eclipsed conformer is calculated to be one‐third lower than for ethane. This decrease is largely attributed to reduced hyperconjugative stabilization of the equilibrium anion conformer compared to that for ethane. Proton removal is also predicted to cause opening of the ethane central CCH angle by 7°, attributed to decreased steric repulsion and to increased hyperconjugative stabilization accompanying angle widening in the ion. © 2004 Wiley Periodicals, Inc. Int J Quantum Chem, 2005