Structural Analysis of Bisphenol-A and its Methylene,Sulfur, and Oxygen Bridged Bisphenol Analogs |
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| Authors: | Caitlin F Lim Joseph M Tanski |
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| Institution: | (1) Department of Chemistry, Vassar College, Box 748, Poughkeepsie, NY 12604, USA |
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| Abstract: | The molecular structures of bisphenol-A, C(CH3)2(p-C6H4OH)2 (monoclinic, P21/n, a = 11.1940(6) Å, b = 18.738(1) Å, c = 17.8623(9) Å, β = 100.571(1)°), its methylene (CH2) and heteroatom (S, O) bridged analogs, CH2(p-C6H4OH)2 (monoclinic, P21/n, a = 5.4351(1) Å, b = 20.7895(3) Å, c = 8.8432(1) Å, β = 93.419(1)°), S(p-C6H4OH)2 (monoclinic, P21/n, a = 5.5115(1) Å, b = 21.0666(2) Å, c = 8.6917(1) Å, β = 92.962(1)°) and O(p-C6H4OH)2 (orthorhombic, Pbcn, a = 5.2745(5) Å, b = 8.2724(8) Å, c = 22.085(2) Å), have been determined by X-ray diffraction at 115 K, revealing structural differences in the series of compounds. The results show that the Caryl–Xbridge–Caryl angles (Xbridge = C(CH3)2, CH2, S, O) span a range greater than 14°. The dihedral angle between the planes of the hydroxyphenyl groups also varies according to the identity of the bridging group, varying from 67.24(2)° in S(p-C6H4OH)2 to 85.82(4)° in C(CH3)2(p-C6H4OH)2. In addition, the pitch angle, which more accurately describes the propeller-like nature of these bisphenolic compounds, varies from 39.88(3)° in S(p-C6H4OH)2 to 59.62(7)° in C(CH3)2(p-C6H4OH)2. Ab initio electronic structure calculations predict very similar bond lengths and angles to those observed crystallographically; however, the predicted dihedral angles and pitch angles are quite different, suggesting that these features are greatly influenced by crystal packing. |
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| Keywords: | Bisphenol-A Bisphenol-F Dihydroxyaryl compounds Molecular structure Dihedral angle Pitch angle Ab initio calculations |
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