caa a22 4500 463184130 CHVBK 20180406164847.0 cr unu---uuuuu 170326e20070901xx s 000 0 eng 10.1007/s10870-007-9207-8 doi (NATIONALLICENCE)springer-10.1007/s10870-007-9207-8 Structural Analysis of Bisphenol-A and its Methylene, Sulfur, and Oxygen Bridged Bisphenol Analogs [Elektronische Daten] [Caitlin Lim, Joseph Tanski] 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 115K, 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. Springer Science+Business Media, LLC, 2007 Bisphenol-A nationallicence Bisphenol-F nationallicence Dihydroxyaryl compounds nationallicence Molecular structure nationallicence Dihedral angle nationallicence Pitch angle nationallicence Ab initio calculations nationallicence Lim Caitlin Department of Chemistry, Vassar College, Box 748, 12604, Poughkeepsie, NY, USA aut Tanski Joseph Department of Chemistry, Vassar College, Box 748, 12604, Poughkeepsie, NY, USA aut Journal of Chemical Crystallography Springer US; http://www.springer-ny.com 37/9(2007-09-01), 587-595 1074-1542 37:9<587 2007 37 10870 https://doi.org/10.1007/s10870-007-9207-8 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/s10870-007-9207-8 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Lim Caitlin Department of Chemistry, Vassar College, Box 748, 12604, Poughkeepsie, NY, USA aut NATIONALLICENCE 700 1- Tanski Joseph Department of Chemistry, Vassar College, Box 748, 12604, Poughkeepsie, NY, USA aut NATIONALLICENCE 773 0- Journal of Chemical Crystallography Springer US; http://www.springer-ny.com 37/9(2007-09-01), 587-595 1074-1542 37:9<587 2007 37 10870 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer