Synthesis and structural analysis of Bis(2-hydroxyphenyl) phenylamine, PhN(o-C6H4OH)2: Comparison with Tris(2-hydroxyphenyl)amine N(o-C6H4OH)3 |
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| Authors: | Bryte V Kelly Joseph M Tanski Mary Beth Anzovino and Gerard Parkin |
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| Institution: | (1) Department of Chemistry, Columbia University, New York, 10027 |
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| Abstract: | The molecular structures of N(o-C6H4OH)3, PhN(o-C6H4OH)2, andp-TolN(o-C6H4OMe)2 have been determined by X-ray diffraction, thereby indicating several structural differences. For example, whereas the nitrogen
in N(o-C6H4OH)3 is pyramidal with ΣC–N–C = 348.3∘, the nitrogen atoms in PhN(o-C6H4OH)2 andp-TolN(o-C6H4OMe)2 are trigonal planar with ΣC–N–C = 359.9∘ and ΣC–N–C = 360.0∘, respectively. The phenyl andp-tolyl groups of PhN(o-C6H4OH)2 andp-TolN(o-C6H4OMe)2 lie close to the trigonal plane, while theo-C6H4OH ando-C6H4OMe groups are almost orthogonal to this plane. The coplanar and orthogonal orientations of the aryl groups of PhN(o-C6H4OH)2 andp-TolN(o-C6H4OMe)2 are in marked contrast to those of the phenyl groups within Ph3N, which exhibit dihedral angles in the range 38–52∘ and approximateD3 symmetry. The observed structures of PhN(o-C6H4OH)2 andp-TolN(o-C6H4OMe)2 may be rationalized in terms of maximizing delocalization of the nitrogen lone pair into the phenyl andp-tolyl groups, while minimizing unfavorable overlap with theo-C6H4OH ando-C6H4OMe groups due to the presence of π-donatingortho-substituents; the orthogonal orientation of theo-C6H4OH ando-C6H4OMe groups is also one that minimizes unfavorable steric interactions between theortho-substituents. |
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| Keywords: | Aryloxide amine phenol tris(2-hydoxyphenyl)amine |
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