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Remote Modulation of Amine Basicity by a Phenylsulfone and a Phenylthio Group
Author(s) -
Martin Rainer E.,
Plancq Baptiste,
Gavelle Olivier,
Wagner Björn,
Fischer Holger,
Bendels Stefanie,
Müller Klaus
Publication year - 2007
Publication title -
chemmedchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.817
H-Index - 100
eISSN - 1860-7187
pISSN - 1860-7179
DOI - 10.1002/cmdc.200600265
Subject(s) - sulfone , amine gas treating , group (periodic table) , chemistry , unit (ring theory) , attenuation , function (biology) , series (stratigraphy) , exponential function , medicinal chemistry , stereochemistry , organic chemistry , mathematics , physics , quantum mechanics , mathematical analysis , mathematics education , paleontology , evolutionary biology , biology
Marked basicity‐lowering effects by a sulfone unit are documented in a series of phenylsulfone amines in which the sulfone unit is placed at different topological distances to an aliphatic amine group. An exponential attenuation of basicity shifts by increasing distance is observed. Smaller effects are exerted by a phenylthio group, in each case corresponding to those of a phenylsulfone unit one σ‐bond further away from the amino function.