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The crystal and molecular structure of an asymmetric diacetylene monomer, 6‐(2‐methyl‐4‐nitroanilino)‐2,4‐hexadiyn‐1‐ol
Author(s) -
Vlasse Marcus,
Paley Mark S.
Publication year - 1994
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/macp.1994.021950810
Subject(s) - diacetylene , monomer , orthorhombic crystal system , polymerization , crystallography , chemistry , crystal structure , polymer chemistry , hydrogen bond , crystal (programming language) , molecule , materials science , polymer , organic chemistry , computer science , programming language
The crystal and molecular structure of an asymmetric diacetylene monomer has been determined from x‐ray diffraction data. The crystals, obtained from an acetone/pentane solution, are orthorhombic, Fdd2 with Z = 16 in a unit cell having dimensions of a = 42,815(6) Å, b = 22,224(5) Å, c = 4,996(1) Å. The structure was solved by direct methods and refined by leastsquares techniques to an R F of 6,4% for 988 reflections and 171 variables. The diacetylene chains are disposed in the unit cell in a complex manner in order to satisfy the hydrogen‐bonding, crystal packing, and symmetry requirements of the system. The solid state polymerization mechanism is discussed with respect to the geometric disposition of the diacetylene chains. These chains are far apart and incorrectly oriented with respect to each other to permit polymerization in the crystal by means of 1,4‐addition, consistent with the Baughman mechanistic model.