In the title compound, trimethoprim trifluoroacetate [or 2,4-diamino-5-(3,4,5-trimethoxybenzyl)pyrimidin-1-ium trifluoroacetate], C14H19N4O3+.C2F3O2-, the trimethoprim molecule is protonated at N-1. The carboxylate group of the trifluoroacetate anion binds with the protonated pyrimidine ring of trimethoprim (TMP) by two nearly parallel N-H...O hydrogen bonds. This is reminiscent of the carboxylate-trimethoprim interaction observed in dihydrofolate reductase (DHFR)-trimethoprim complexes. The pyrimidine moieties of the trimethoprim cations are centrosymmetrically paired through a pair of N-H...N hydrogen bonds involving the 4-amino group and atom N3. The 2-amino group of one TMP motif and the 4-amino group of another motif (both of these motifs are members of a base pair) are bridged by one of the methoxy O atom of a third TMP motif, leading to a five-membered (excluding H atoms) hydrogen-bonded chelate. One of the H atoms of the 2-amino group is also involved in a bifurcated hydrogen bond involving two methoxy O atoms of a trimethoprim motif, leading to a five-membered (including the H atom) hydrogen-bonded chelate. The pyrimidine ring makes a dihedral angle of 83.69 (10)degrees with the phenyl ring in the trimethoprim cation. In the trifluoroacetate moiety, the average F-C bond distance is 1.261 Angstrom and F-C-C and F- C-F bond angles are 114.7 and 103.7degrees respectively.

Hydrogen-bonding patterns in trimethoprim trifluoroacetate / Francis, S.; Muthiah, P. T.; Bocelli, G.; Righi, Lara. - In: ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE. - ISSN 1600-5368. - 58:(2002), pp. o717-o719. [10.1107/S1600536802009509]

Hydrogen-bonding patterns in trimethoprim trifluoroacetate

RIGHI, Lara
2002

Abstract

In the title compound, trimethoprim trifluoroacetate [or 2,4-diamino-5-(3,4,5-trimethoxybenzyl)pyrimidin-1-ium trifluoroacetate], C14H19N4O3+.C2F3O2-, the trimethoprim molecule is protonated at N-1. The carboxylate group of the trifluoroacetate anion binds with the protonated pyrimidine ring of trimethoprim (TMP) by two nearly parallel N-H...O hydrogen bonds. This is reminiscent of the carboxylate-trimethoprim interaction observed in dihydrofolate reductase (DHFR)-trimethoprim complexes. The pyrimidine moieties of the trimethoprim cations are centrosymmetrically paired through a pair of N-H...N hydrogen bonds involving the 4-amino group and atom N3. The 2-amino group of one TMP motif and the 4-amino group of another motif (both of these motifs are members of a base pair) are bridged by one of the methoxy O atom of a third TMP motif, leading to a five-membered (excluding H atoms) hydrogen-bonded chelate. One of the H atoms of the 2-amino group is also involved in a bifurcated hydrogen bond involving two methoxy O atoms of a trimethoprim motif, leading to a five-membered (including the H atom) hydrogen-bonded chelate. The pyrimidine ring makes a dihedral angle of 83.69 (10)degrees with the phenyl ring in the trimethoprim cation. In the trifluoroacetate moiety, the average F-C bond distance is 1.261 Angstrom and F-C-C and F- C-F bond angles are 114.7 and 103.7degrees respectively.
Hydrogen-bonding patterns in trimethoprim trifluoroacetate / Francis, S.; Muthiah, P. T.; Bocelli, G.; Righi, Lara. - In: ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE. - ISSN 1600-5368. - 58:(2002), pp. o717-o719. [10.1107/S1600536802009509]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11381/1460137
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