Computational Study of the One- and Two-Dimensional Infrared Spectra of a Proton-Transfer Mode in a Hydrogen-Bonded Complex Dissolved in a Polar Nanocluster

ChemPhysChem ◽  
2013 ◽  
Vol 14 (14) ◽  
pp. 3309-3318 ◽  
Author(s):  
Chia Shen Sow ◽  
Joseph Tomkins ◽  
Gabriel Hanna
Keyword(s):  
Proton Transfer ◽  
Infrared Spectra ◽  
Computational Study ◽  
Two Dimensional ◽  
Transfer Mode ◽  
The One ◽  
Hydrogen Bonded

Bis{4-[(4-pyridyl)ethenyl]pyridinium} 4-sulfonatobenzoate trihydrate

2006 ◽  
Vol 62 (4) ◽  
pp. o1529-o1531 ◽  
Author(s):  
Li-Ping Zhang ◽  
Long-Guan Zhu
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Proton Transfer ◽  
Water Molecules ◽  
Stacking Interactions ◽  
Two Dimensional ◽  
One Dimensional ◽  
Π Stacking ◽  
Dimensional Network ◽  
Hydrogen Bonded

In the crystal structure of the title organic proton-transfer complex, 2C12H11N2 +·C7H4O5S2−·3H2O, the cations form one-dimensional chains via intermolecular N—H...N hydrogen bonds and these chains, in turn, form a two-dimensional network through π–π stacking interactions. In addition, the anions and water molecules are connected into a two-dimensional hydrogen-bonded network through intermolecular O—H...O hydrogen bonds. The two motifs result in sheets of cations and anions stacked alternately.

scholarly journals Zero-, one- and two-dimensional hydrogen-bonded structures in the 1:1 proton-transfer compounds of 4,5-dichlorophthalic acid with the monocyclic heteroaromatic Lewis bases 2-aminopyrimidine, nicotinamide and isonicotinamide

2009 ◽  
Vol 65 (3) ◽  
pp. o103-o107 ◽  
Author(s):  
Graham Smith ◽  
Urs D. Wermuth ◽  
Jonathan M. White
Keyword(s):  
Proton Transfer ◽  
Lewis Base ◽  
Two Dimensional ◽  
Compound I ◽  
Lewis Bases ◽  
Amide Carbonyl ◽  
Low Dimensionality ◽  
Low Dimensional ◽  
Proton Transfer Compounds ◽  
Hydrogen Bonded

The structures of the anhydrous 1:1 proton-transfer compounds of 4,5-dichlorophthalic acid (DCPA) with the monocyclic heteroaromatic Lewis bases 2-aminopyrimidine, 3-(aminocarbonyl)pyridine (nicotinamide) and 4-(aminocarbonyl)pyridine (isonicotinamide), namely 2-aminopyrimidinium 2-carboxy-4,5-dichlorobenzoate, C4H6N3+·C8H3Cl2O4−, (I), 3-(aminocarbonyl)pyridinium 2-carboxy-4,5-dichlorobenzoate, C6H7N2O+·C8H3Cl2O4−, (II), and the unusual salt adduct 4-(aminocarbonyl)pyridinium 2-carboxy-4,5-dichlorobenzoate–methyl 2-carboxy-4,5-dichlorobenzoate (1/1), C6H7N2O+·C8H3Cl2O4−·C9H6Cl2O4, (III), have been determined at 130 K. Compound (I) forms discrete centrosymmetric hydrogen-bonded cyclic bis(cation–anion) units having bothR22(8) andR12(4) N—H...O interactions. In (II), the primary N—H...O-linked cation–anion units are extended into a two-dimensional sheet structureviaamide–carboxyl and amide–carbonyl N—H...O interactions. The structure of (III) reveals the presence of an unusual and unexpected self-synthesized methyl monoester of the acid as an adduct molecule, giving one-dimensional hydrogen-bonded chains. In all three structures, the hydrogen phthalate anions are essentially planar with short intramolecular carboxyl–carboxylate O—H...O hydrogen bonds [O...O = 2.393 (8)–2.410 (2) Å]. This work provides examples of low-dimensional 1:1 hydrogen-bonded DCPA structure types, and includes the first example of a discrete cyclic `heterotetramer.' This low dimensionality in the structures of the 1:1 aromatic Lewis base salts of the parent acid is generally associated with the planar DCPA anion species.

Patterns of hydrogen bonding in mono- and di-substituted N-arylpyrazinecarboxamides

2008 ◽  
Vol 64 (1) ◽  
pp. 84-100 ◽  
Author(s):  
Solange M. S. V. Wardell ◽  
Marcus V. N. de Souza ◽  
Thatyana R. A. Vasconcelos ◽  
Marcelle de L. Ferreira ◽  
James L. Wardell ◽  
...  
Keyword(s):  
Hydrogen Bonds ◽  
Three Dimensional ◽  
Intermolecular Forces ◽  
Supramolecular Structures ◽  
Two Dimensional ◽  
Π Stacking ◽  
Compact Range ◽  
Wide Range ◽  
The One ◽  
Hydrogen Bonded

The molecular and supramolecular structures of 18 N-arylpyrazinecarboxamides, Ar NHCO(C4H3N2), have been determined, including the stoichiometric monohydrate of N-(3-methoxyphenyl)pyrazinecarboxamide, and two polymorphs of N-(4-fluorophenyl)pyrazinecarboxamide having Z′ values of 1 and 4, respectively. The aryl groups were selected to include the geometric isomers for a compact range of substituents, namely methyl, trifluoromethyl, fluoro, chloro, methoxy and nitro groups, which exhibit markedly varied electronic properties and markedly varied behaviour as hydrogen-bond donors and acceptors. However, not all isomers in each group could be structurally investigated. A small number of derivatives containing disubstituted aryl groups have also been included in this study. The crystal structures of the solvent-free carboxamides reported here exhibit a wide range of direction-specific intermolecular forces, including N—H...N, N—H...O, C—H...N and C—H...O hydrogen bonds, and π...π stacking interactions, while the structure of N-(3-methoxyphenyl)pyrazinecarboxamide monohydrate also contains O—H...N and O—H...O hydrogen bonds. The resulting supramolecular structures can be zero-, one- or two-dimensional, although no three-dimensional supramolecular aggregation has been observed. In the finite, zero-dimensional structures, pairs of molecules are linked by hydrogen bonds to form cyclic centrosymmetric dimers. The one-dimensional structures include chains formed by the π-stacking of otherwise isolated molecules, simple chains generated by either C—H...O or C—H...N hydrogen bonds, and hydrogen-bonded chains of rings. The two-dimensional structures include examples of both π-stacked hydrogen-bonded chains and hydrogen-bonded sheets.

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