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Influence of Strong Transannular N→P Interaction on Acidity of Cyclenphosphine Sulfide
Author(s) -
DéchampsOlivier Isabelle,
Barbier JeanPierre,
Aplincourt Michel,
Oget Nicolas,
Chuburu Françoise,
Handel Henri
Publication year - 1999
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/(sici)1522-2675(19990505)82:5<790::aid-hlca790>3.0.co;2-g
Subject(s) - chemistry , deprotonation , sulfide , aqueous solution , base (topology) , acid–base reaction , medicinal chemistry , inorganic chemistry , stereochemistry , computational chemistry , organic chemistry , ion , mathematical analysis , mathematics
Abstract The acid‐base behavior of cyclenphosphine sulfide (cyclenPS) is appreciably different from that of cyclamphosphine sulfide (cyclamPS). The cyclenPS shows five acid functionalities compared to four for cyclamPS. The fifth acidic group in cyclenPS corresponds to the formation of a stable amidure in aqueous solution (p K a 5=12.3). This behavior is due to the strong transannular N→P interaction. The deprotonation sequences were established by 31 P‐NMR and confirmed by modelling of cyclenPS.