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Phosphonic systems. Part 8. Solution and solid‐state conformation of diastereomeric adducts of diethyl prop‐2‐enylphosphonate to p ‐nitrobenzaldehyde
Author(s) -
Müller Elmar L.,
Roos H. Marita,
Modro Tomasz A.
Publication year - 1993
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/poc.610060111
Subject(s) - chemistry , diastereomer , conformational isomerism , intramolecular force , adduct , solid state , intermolecular force , hydrogen bond , molecule , crystal structure , molecular conformation , stereochemistry , crystallography , organic chemistry
A mixture of siastereomeric adducts of lithiated diethyl prop‐2‐enylphosphonate to p ‐nitrobenzaldehyde was separated and the solution and the solid‐state structures of the individual stereoisomers were studied. Conformational analysis demonstrated that in solution the most populated rotamer involves in both cases trans orientation of the PO 3 Et 2 and O 2 NC 6 H 4 groups and a gauche relationship of the phosphoryl and hydroxyl groups. In the solid state the crystal structure determination demonstrated that the molecules exist in the same conformation as in solution, although the PO ⃛HO hydrogen bonding changed from intramolecular to intermolecular (dimeric) interactions.