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Effect of intramolecular interactions on circular dichroism of ortho‐substituted 1‐phenethylamines
Author(s) -
Demyanovich V.M.,
Shishkina I.N.,
Zefirov N.S.
Publication year - 2004
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20057
Subject(s) - chemistry , intramolecular force , phenethylamines , circular dichroism , hydrogen bond , stereochemistry , chirality (physics) , vibrational circular dichroism , computational chemistry , molecule , organic chemistry , chiral symmetry , physics , quantum mechanics , nambu–jona lasinio model , quark
The synthesis of ortho‐substituted (S)‐1‐phenethylamines via ortho‐lithiation of its N,N‐dimethyl derivative followed by reactions with different reagents is described. Circular dichroism spectra of synthesized compounds were measured. It is shown that the observed short‐wave Cotton effects greatly depend on the existence of cyclic structure due to possible interactions such as hydrogen bond or electrostatic interaction. Chirality 16:486–492, 2004. © 2004 Wiley‐Liss, Inc.