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Synthesis and structural analysis of Bis(2-hydroxyphenyl) phenylamine, PhN(o-CHOH): Comparison with Tris(2-hydroxyphenyl)amine N(o-CHOH)

Journal of Chemical Crystallography, ISSN: 1074-1542, Vol: 35, Issue: 12, Page: 969-981
2005
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The molecular structures of N(o-CHOH), PhN(o-CHOH), and p-TolN(o-C HOMc) have been determined by X-ray diffraction, thereby indicating several structural differences. For example, whereas the nitrogen in N(o-CHOH) is pyramidal with ∑ = 348.3°, the nitrogen atoms in PhN(o-CHOH) and p-TolN(o-CH OMe) are trigonal planar with ∑ = 359.9° and ∑ = 360.0°, respectively. The phenyl and p-tolyl groups of PhN(o-CHOH) and p-TolN(o-CHOMe) lie close to the trigonal plane, while the o-CHOH and o-CH OMe groups are almost orthogonal to this plane. The coplanar and orthogonal orientations of the aryl groups of PhN(o-CH OH) and p-TolN(o-CHOMe) are in marked contrast to those of the phenyl groups within Ph N, which exhibit dihedral angles in the range 38-52° and approximate D symmetry. The observed structures of PhN(o-C HOH) and p-TolN(o-CH OMe) may be rationalized in terms of maximizing delocalization of the nitrogen lone pair into the phenyl and p-tolyl groups, while minimizing unfavorable overlap with the o-CHOH and o-CHOMe groups due to the presence of π-donating ortho-substituents; the orthogonal orientation of the o-CH OH and o-CHOMe groups is also one that minimizes unfavorable steric interactions between the ortho-substituents. © 2005 Springer Science+Business Media, Inc.

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