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Electronic structure of N ‐sulfenylimines
Author(s) -
Bharatam Prasad V.,
Kaur Damanjit
Publication year - 2003
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.592
Subject(s) - chemistry , natural bond orbital , ab initio , computational chemistry , sulfur , anomeric effect , bond length , crystallography , nitrogen , density functional theory , anomer , stereochemistry , organic chemistry , crystal structure
The electronic structure of N ‐sulfenylimines was studied in detail using ab initio MO and density functional methods. The S—N rotational barriers and N‐inversion barriers in HS—NCH 2 at the G2MP2 level were found to be 5.60 and 21.76 kcal mol −1 , respectively. There is a partial pπ–pπ bond and a relatively weak n N → σ* S—R anomeric π bond between sulfur and nitrogen in N ‐sulfenylimines. NBO analysis was carried out to estimate quantitatively the above delocalizations in RS—NCH 2 (R = H, Me, Cl, F, BH 2 ) systems. Copyright © 2003 John Wiley & Sons, Ltd.
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