Hydrogen bond studies. A neutron diffraction study of the structures of succinic acid at 300 and 77 K

Leviel, J.L.; Auvert, G.; Savariault, Jean‐Michel

doi:10.1107/s0567740881008352

Cited by 63 publications

(34 citation statements)

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“…In the eight crystallographically independent carboxyl groups in the complexes in which the hydrogen atom has been located, five have the cis conformation while the remaining three have the trans conformation. The hydrogen atom is also located in the cis position in the two crystal structures containing succinic acid reported earlier (Huang, Leiserowitz & Schmitt, 1973;Leviel, Auvert & Savariault, 1981).…”

Section: Succinic Acid Conformationmentioning

confidence: 87%

X-ray studies on crystalline complexes involving amino acids and peptides. XXV. Structures of DL-proline hemisuccinic acid and glycyl-L-histidinium semisuccinate monohydrate and a comparative study of amino-acid and peptide complexes of succinic acid

Prasad¹,

Vijayan²

1993

Acta Crystallogr Sect B

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(1), Dx = 1.48 g cm -3, R =0.027 for 1610 observed reflections. Normal amino-acid and dipeptide aggregation patterns are preserved in the structures in spite of the presence of succinic acid/semisuccinate ions. In both the structures, the amino-acid/dipeptide layers stack in such a way that the succinic acid molecules/semisuccinate ions are enclosed in voids created during stacking. Substantial variability in the ionization state and the stoichiometry is observed in amino-acid and peptide complexes of succinic acid. Succinic acid molecules and succinate ions appear to prefer a planar centrosymmetric conformation with the two carboxyl (carboxylate) groups trans with respect to the central C--C bond. Considerable variation is seen in the departure from and modification of normal aminoacid aggregation patterns produced by the presence of succinic acid. Some of the complexes can be described as inclusion compounds with the amino acid/dipeptide as the 'host' and succinic acid/ semisuccinate/succinate as the 'guest'. The effects of change in chirality, though very substantial, are not the same in different pairs of complexes involving DL and L isomers of the same amino acid.

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Section: Succinic Acid Conformationmentioning

confidence: 87%

X-ray studies on crystalline complexes involving amino acids and peptides. XXV. Structures of DL-proline hemisuccinic acid and glycyl-L-histidinium semisuccinate monohydrate and a comparative study of amino-acid and peptide complexes of succinic acid

Prasad¹,

Vijayan²

1993

Acta Crystallogr Sect B

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“…. Y telle qu'elle est mesurCe aux neutrons ou rayons X n'est pas du tout suffisante pour expliquer cette d6rive di;,/dT (4,22). C'est un resultat interessant, car il permet de decrire avec precision la sensibilitC thermique de certaines propriCtCs de la LH, ce qui peut avoir un impact non nkgligeable en biologie.…”

Section: Analyse De La Bande Vunclassified

La mécanique de la liaison hydrogène: résultats de spectroscopie infrarouge

Maréchal¹

1985

Can. J. Chem.

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We review the mechanics of H-bonds as revealed by ir spectroscopy and show how the various (strong) anharmonic couplings of the νs vibrations [Formula: see text]of H-bonds may be treated so as to eliminate the irrelevant features of the spectra and keep only those features which may give information on the still unknown dynamical quantities of the H-bonds, such as the transfer of protons through H-bonds or the mechanism of rupture of H-bonds. We also describe the possibilities offered by vibrational spectroscopy for studying these dynamical quantities, which may be important in biology.

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“…23 For this reason our experiment has been supplemented with theoretical calculations intended to test the accuracy of different methods and basis sets. Previous neutron diffraction data for crystalline succinic acid are available 24 and show that the molecule is essentially planar and forms linear chains via hydrogen bonds in the crystal. In the presence of crystal lattice strain, it assumes a trans conformation about the central C2-C3 bond, in contrast to the gauche skeleton predicted by quantum calculations of the isolated molecule.…”

Section: Introductionmentioning

confidence: 99%

Conformational steering in dicarboxy acids: the native structure of succinic acid

Jahn

Méndez

Nair

et al. 2015

Phys. Chem. Chem. Phys.

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The torsional freedom of the carbon backbone and hydroxyl groups of succinic acid, an important platform chemical fi nding numerous industrial applications as well as being the focus of considerable research in atmospheric science, is elucidated. The question of the potential presence of numerous conformers is answered by an unambiguous identifi cation of the structural and molecular properties using microwave and millimeter wave spectroscopy. The precise spectroscopic data provides evidence that the anomalous tendency of "folding the methylene unit" is favoured. Succinic acid, a dicarboxylic acid molecule, has been investigated spectroscopically with computational support to elucidate the complex aspects of its conformational composition. Due to the torsional freedom of the carbon backbone and hydroxy groups, a large number of potentially plausible conformers can be generated with an indication that the gauche conformer is favored over the trans form. The microwave and millimeter wave spectra have been analyzed and accurate spectroscopic constants have been derived that correlate best with those of the lowest energy gauche conformer. For an unambiguous conformational identification measurements were extended to the monosubstituted isotopologues, precisely determining the structural properties. Besides bond distances and angles, particularly the dihedral angle has been determined to be 67.76(11)1, confirming the anomalous tendency of the methylene units to favor gauche conformers when a short aliphatic segment is placed between two carbonyl groups.

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Hydrogen bond studies. A neutron diffraction study of the structures of succinic acid at 300 and 77 K

Cited by 63 publications

References 1 publication

X-ray studies on crystalline complexes involving amino acids and peptides. XXV. Structures of DL-proline hemisuccinic acid and glycyl-L-histidinium semisuccinate monohydrate and a comparative study of amino-acid and peptide complexes of succinic acid

X-ray studies on crystalline complexes involving amino acids and peptides. XXV. Structures of DL-proline hemisuccinic acid and glycyl-L-histidinium semisuccinate monohydrate and a comparative study of amino-acid and peptide complexes of succinic acid

La mécanique de la liaison hydrogène: résultats de spectroscopie infrarouge

Conformational steering in dicarboxy acids: the native structure of succinic acid

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