Influence of strong transannular N -> P interaction on acidity of cyclenphosphine sulfide

Authors
Dechamps-Olivier, I Barbier, JP Aplincourt, M Oget, N Chuburu, F Handel, H
Citation
I. Dechamps-olivier et al., Influence of strong transannular N -> P interaction on acidity of cyclenphosphine sulfide, HELV CHIM A, 82(5), 1999, pp. 790-795
Citations number
11
Categorie Soggetti
Chemistry & Analysis",Chemistry
Journal title
HELVETICA CHIMICA ACTA
ISSN journal
0018019X → ACNP
Volume
82
Issue
5
Year of publication
1999
Pages
790 - 795
Database
ISI
SICI code
0018-019X(1999)82:5<790:IOSTN->2.0.ZU;2-W
Abstract
The acid-base behavior of cyclenphosphine sulfide (cyclenPS) is appreciably different from that of cyclamphosphine sulfide (cyclamPS). The cyclenPS sh ows five acid functionalities compared to four for cyclamPS. The filth acid ic group in cyclenPS corresponds to the formation of a stable amidure in aq ueous solution (pK(a) = 12.3). This behavior is due to the strong transannu lar N - P interaction. The deprotonation sequences were established by P-31 -NMR and confirmed by modelling of cyclenPS.