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Structural studies of phosphoramidates. Conformational preferences and hydrogen bonding
Author(s) -
Wan Huijie,
Modro Agnes M.,
Modro Tom A.,
Bourne Susan,
Nassimbeni Luigi R.
Publication year - 1996
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/(sici)1099-1395(199611)9:11<739::aid-poc836>3.0.co;2-k
Subject(s) - chemistry , diastereomer , hydrogen bond , molecule , single bond , torsion (gastropod) , crystallography , substrate (aquarium) , molecular conformation , stereochemistry , computational chemistry , organic chemistry , medicine , alkyl , oceanography , surgery , geology
The x‐ray molecular structures of five chiral phosphoramidates derived from N ‐phosphorylated nitrogen mustard were determined and the molecular parameters are discussed. The value of the torsion angle of the O(SINGLE BOND)P(SINGLE BOND)N(SINGLE BOND)H function which determines the packing of the molecules was found to determine also the ability of a substrate to form diastereomeric hydrogen‐bonded complexes with optically active acids.