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Effects of sulfenyl, sulfinyl and sulfonyl groups on acidities and homolytic bond dissociation energies of adjacent C-H and N-H bonds
Journal of physical organic chemistry, 1998-06, Vol.11 (6), p.397-406
Bordwell, Frederick G.
Liu, Wei-Zhong
1998
Details
Autor(en) / Beteiligte
Bordwell, Frederick G.
Liu, Wei-Zhong
Titel
Effects of sulfenyl, sulfinyl and sulfonyl groups on acidities and homolytic bond dissociation energies of adjacent C-H and N-H bonds
Ist Teil von
Journal of physical organic chemistry, 1998-06, Vol.11 (6), p.397-406
Ort / Verlag
Chichester, UK: John Wiley & Sons, Ltd
Erscheinungsjahr
1998
Link zum Volltext
Quelle
Wiley Online Library - AutoHoldings Journals
Beschreibungen/Notizen
Acidities and bond dissociation energies (BDEs) of the N–H bond in two phenylsulfenylamides, PhSNHBz and PhSNH‐t‐Bu, and four phenylsulfenylanilides, 4‐GC6H4NHSPh, where G = MeO, H, Br and CN, were measured in order to compare the effects of substituents on acidities and BDEs of N—H bonds with those of C—H bonds. The effects of PhS groups on acidities and BDEs in a series of C—H acids were found to be comparable to those on acidities and BDEs of PhS in a similar series of N—H acids. Comparisons were also made of the effects of changing the oxidation state of sulfur in the series PhS, PhSO and PhSO2 on the acidities and BDEs of adjacent N—H and C—H bonds in weak acids. Hammett‐type plots of pKHA values for phenyl benzyl sulfones (4‐GC6H4CH2SO2Ph) and phenylsulfenylanilides (4‐GC6H4NHSPh) were linear vs σp− values. A linear plot was obtained and explained for a plot of BDE of the N—H bonds in remotely substituted phenylsulfonylanilides with σ+ values. Plots of BDEs vs Eox(A−) were also linear for 4‐substituted phenylsulfenylanilides (4‐GC6H4NHSPh), phenylsulfonylanilides (4‐GC6H4NHSO2Ph) and phenyl benzyl sulfones (4‐GC6H4CH2SO2Ph). © 1998 John Wiley & Sons, Ltd.
Sprache
Englisch
Identifikatoren
ISSN: 0894-3230
eISSN: 1099-1395
DOI: 10.1002/(SICI)1099-1395(199806)11:6<397::AID-POC10>3.0.CO;2-B
Titel-ID: cdi_crossref_primary_10_1002__SICI_1099_1395_199806_11_6_397__AID_POC10_3_0_CO_2_B
Format
–
Schlagworte
acidity
,
bond dissociation energy
,
phenylsulfenylamides
,
phenylsulfenylanilides
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