Sigalov Mark V, Shainyan Bagrat A, Chipanina Nina N, Oznobikhina Larisa P
Department of Chemistry, Ben-Gurion University of the Negev , 84105 Beer-Sheva, Israel.
J Phys Chem A. 2013 Nov 7;117(44):11346-56. doi: 10.1021/jp4072179. Epub 2013 Oct 24.
The series of push-pull compounds containing the pyrrole ring as a donor and the 1,3-indandione derived moieties as the acceptor unit were synthesized, and strong intramolecular hydrogen bonding in their molecules was studied. In the presence of fluoride and acetate anions their solutions undergo color changes. It was shown by NMR, UV-vis, and quantum chemical calculations including AIM analysis that all these compounds undergo solvent-assisted rupture of the intramolecular hydrogen bond followed by the formation of a strong intermolecular hydrogen bond with fluoride and acetate anions which finally abstract a proton from the pyrrole ring. The insensitivity of the studied compounds to other anions (Cl, Br, HSO4, PF6) is consequence of the instability of the corresponding hydrogen-bonded complexes.
合成了一系列以吡咯环为供体、1,3-茚二酮衍生部分为受体单元的推拉型化合物，并研究了其分子内的强氢键。在氟离子和醋酸根阴离子存在下，它们的溶液会发生颜色变化。通过核磁共振（NMR）、紫外可见光谱（UV-vis）以及包括原子间相互作用分子轨道（AIM）分析在内的量子化学计算表明，所有这些化合物都会经历分子内氢键的溶剂辅助断裂，随后与氟离子和醋酸根阴离子形成强分子间氢键，最终从吡咯环夺取一个质子。所研究的化合物对其他阴离子（氯离子、溴离子、硫酸氢根离子、六氟磷酸根离子）不敏感，是相应氢键配合物不稳定的结果。
