Premium
Chiral ureas with two electronegative substituents at 1‐N: An unusual case of coexisting pyramidal and almost planar 1‐N atoms in the same crystal
Author(s) -
Shishkin Oleg V.,
Shtamburg Vasiliy G.,
Zubatyuk Roman I.,
Olefir Dmitriy A.,
Tsygankov Alexander V.,
Prosyanik Alexander V.,
Mazepa Alexander V.,
Kostyanovsky Remir G.
Publication year - 2009
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.20668
Subject(s) - chemistry , crystallography , alkoxy group , nitrogen atom , anomer , crystal structure , crystal (programming language) , stereochemistry , anomeric effect , nitrogen , group (periodic table) , atom (system on chip) , ring (chemistry) , alkyl , organic chemistry , computer science , programming language , embedded system
XRD studies of structure of N ‐acetoxy‐ N ‐methoxyurea and N , N ‐bis(methoxycarbonyl)‐ N ‐methoxyimide have revealed that in N ‐methoxy‐ N ‐X‐ureas (X = OAc, Cl, OMe, N + C 5 H 5 ) the additional shortening of NOMe bond took place, which arising from an n O(Me) ‐σ* NX anomeric orbital interaction. XRD studies of N ‐chloro‐ N ‐ethoxyurea crystal have revealed the presence of two kinds of anomeric nitrogen configuration in the ONCl group in the form of a pyramidal configuration and a planar configuration for same 1‐N nitrogen atom. XRD studies of N ‐4‐chlorobenzoyloxy‐ N ‐ethoxyurea have revealed that the degree of pyramidality of the 1‐N nitrogen in N ‐aroyloxy‐ N ‐alkoxyureas is tuned by orientation of benzoyl group with respect to the NO bond, which in turn depends of size of N ‐alkoxy group. Chirality, 2009. © 2008 Wiley‐Liss, Inc.