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Conformation and dynamics in a solution of an N ‐quaternized cinnamide derivative: A molecule active as a UV filter
Author(s) -
Anselmi Cecilia,
Centini Marisanna,
Scotton Mirella,
Sega Alessandro
Publication year - 1992
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.1260301005
Subject(s) - chemistry , moiety , alkyl , molecule , bromide , relaxation (psychology) , stereochemistry , computational chemistry , crystallography , medicinal chemistry , organic chemistry , social psychology , psychology
The dynamics and conformation of N , N ‐dimethyl‐ N ‐[3‐(4‐methoxy‐trans‐cinnamoylamino)propyl]‐ N ‐ n ‐dodecylammonium bromide (1) have been established in two solvents (CDCl 3 and DMSO‐ d 6 ) by the use of 13 C spin–lattice relaxation rates, non‐selective and selective proton spin–lattice relaxation rates and 1 H–( 1 H) NOE experiments. The two solvents affect the conformation of the cinnamide moiety in different ways. This alters the anchor capacity of the moiety towards the alkyl chain and, as a consequence, the dynamics of 1 in CDCl 3 and DMSO‐ d 6 show understandable differences. However, the main mean conformations of 1 in both solvents are ‘linear’. The data do not allow the rationalization of the relationship between conformation and sunscreen efficiency.