TY - JOUR
T1 - Stabilization of a high energy molecular conformation by specific intermolecular forces, a novel planar benzylideneaniline system
AU - Navon, Oshrit
AU - Bernstein, Joel
N1 - Funding Information:
Partial support from the United States-Israel Binational Science Foundation (BSF, Jerusalem) (Grant No. 94-00394(1)) and the Germany-Israel Foundation (GIF) (Grant No. I 0333-263.06/93) is gratefully acknowledged. We also wish to thank Drs. Arkady Ellem and Sharona Zamir for assistance and encouragement.
PY - 1997/1/1
Y1 - 1997/1/1
N2 - The system containing six benzylideneanilines (BA) has been studied: Group 1: I: N-(p-Chlorobenzylideneaniline)m-chloroaniline (BA, X = 4 - Cl, Y = 3 - Cl) II: N-(p-Bromobenzylideneaniline)m-bromoaniline (BA, X = 4 - Br, Y = 3 - Br) III: N-(p-Bromobenzylideneaniline)m-chloroaniline (BA, X = 4 - Br, Y = 3 - Cl) IV: N-(p-Chlorobenzylideneaniline)m-bromoaniline (BA, X = 4 - Cl, Y = 3 - Br) Group 2: V: N-(m-Chlorobenzylideneaniline)p-bromoaniline (BA, X = 3 - Cl, Y = 4 - Br) VI: N-(m-Bromobenzylideneaniline)p-chloroaniline (BA, X = 3 - Br, Y = 4 - Br) The crystal structures of Group 1 are isostructural. They crystallize in a monoclinic cell, space group P2l. They are rare examples of planar benzylideneanilines in a nondisordered crystal structure. The crystal structures exhibit an intermolecular ring containing five atoms and hal - hal, C - H - hal interactions, which may contribute to the planarity of the molecule. The structures in Group 2 crystallize in a monoclinic cell, space group P2l/c. The conformation is nonplanar and there are no intermolecular halogen - halogen interactions. The abovementioned live atom pattern ring does not occur in these structures. These two groups of structures show that the type and mode of molecular substitution can lead to specific intermolecular interactions which in turn stabilize an otherwise unfavorable molecular conformation.
AB - The system containing six benzylideneanilines (BA) has been studied: Group 1: I: N-(p-Chlorobenzylideneaniline)m-chloroaniline (BA, X = 4 - Cl, Y = 3 - Cl) II: N-(p-Bromobenzylideneaniline)m-bromoaniline (BA, X = 4 - Br, Y = 3 - Br) III: N-(p-Bromobenzylideneaniline)m-chloroaniline (BA, X = 4 - Br, Y = 3 - Cl) IV: N-(p-Chlorobenzylideneaniline)m-bromoaniline (BA, X = 4 - Cl, Y = 3 - Br) Group 2: V: N-(m-Chlorobenzylideneaniline)p-bromoaniline (BA, X = 3 - Cl, Y = 4 - Br) VI: N-(m-Bromobenzylideneaniline)p-chloroaniline (BA, X = 3 - Br, Y = 4 - Br) The crystal structures of Group 1 are isostructural. They crystallize in a monoclinic cell, space group P2l. They are rare examples of planar benzylideneanilines in a nondisordered crystal structure. The crystal structures exhibit an intermolecular ring containing five atoms and hal - hal, C - H - hal interactions, which may contribute to the planarity of the molecule. The structures in Group 2 crystallize in a monoclinic cell, space group P2l/c. The conformation is nonplanar and there are no intermolecular halogen - halogen interactions. The abovementioned live atom pattern ring does not occur in these structures. These two groups of structures show that the type and mode of molecular substitution can lead to specific intermolecular interactions which in turn stabilize an otherwise unfavorable molecular conformation.
KW - Benzylideneaniline
KW - Intermolecular forces
KW - Molecular conformation
UR - http://www.scopus.com/inward/record.url?scp=3543077719&partnerID=8YFLogxK
U2 - 10.1007/BF02272342
DO - 10.1007/BF02272342
M3 - Article
AN - SCOPUS:3543077719
SN - 1040-0400
VL - 8
SP - 3
EP - 11
JO - Structural Chemistry
JF - Structural Chemistry
IS - 1
ER -