Low Barrier Hydrogen Bond (LBHB) Interactions in the Solid State Crystal Structures of Phthalate Salts Based on Trisubstituted Guanidinium Cations
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Keywords

N, N', N''- Tricyclohexylguanidinium hydrogen phthalate; Hydrogen-Bonding; Intermolecular and intramolecular interactions.

How to Cite

Said, F. (2012). Low Barrier Hydrogen Bond (LBHB) Interactions in the Solid State Crystal Structures of Phthalate Salts Based on Trisubstituted Guanidinium Cations. Jordan Journal of Chemistry (JJC), 7(3), 297-309. Retrieved from http://jjc.yu.edu.jo/index.php/jjc/article/view/209

Abstract

The hydrogen phthalate salt N, N', N''- tricyclohexylguanidinium hydrogen phthalate {C(HNcyclohexyl)3}+HPHT-(1) was prepared and the structure was determined by X-ray diffraction analysis and characterized by elemental analysis, NMR and IR spectroscopy. The hydrogen-bonding interactions of this colorless solid have been explored in order to examine the potential of intermolecular and intramolecular interactions and their influence on the extended structure that was observed. Compound 1 crystallizes in the monoclinic space group P2(1)/n, with a = 10.6270 (13) Ă, b = 16.809 (2) Ă, c = 15.1657 (18) Ă and β = 102.978 (2)º; Z = 4. The crystal data indicate that the anion displayed a characteristic intramolecular, low barrier hydrogen bond (LBHB) (S(7) motif) via O-HO interaction. The primary structure combines two cyclic associations, a 16-membered ring (R44(16) notation) and a large 46-membered ring (R44(46) notation), through N-H…O hydrogen-bonding interactions. The structure of 1 is compared with the analogue salts N, N', N''- triisopropylguanidinium phthalate 2 and N, N', N''- triisopropylguanidinium hydrogen maleate 3.

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