Understanding the influence of low-frequency vibrations on the hydrogen bonds of acetic acid and acetamide dimers

2017 ◽  
Vol 19 (36) ◽  
pp. 24866-24878 ◽  
Author(s):  
Christopher Copeland ◽  
Omkaran Menon ◽  
D. Majumdar ◽  
Szczepan Roszak ◽  
Jerzy Leszczynski
Keyword(s):  
Hydrogen Bond ◽  
Acetic Acid ◽  
Hydrogen Bonds ◽  
High Frequency ◽  
Low Frequency ◽  
Weakly Interacting ◽  
Bond Strengths ◽  
High Frequency Modes

Low-frequency vibrations coupled to high-frequency modes are known to influence the hydrogen bond strengths in a weakly interacting dimer.

scholarly journals A new solvate of epalerstat, a drug for diabetic neuropathy

2017 ◽  
Vol 73 (8) ◽  
pp. 1264-1267 ◽  
Author(s):  
Okky Dwichandra Putra ◽  
Daiki Umeda ◽  
Kaori Fukuzawa ◽  
Mihoko Gunji ◽  
Etsuo Yonemochi
Keyword(s):  
Hydrogen Bond ◽  
Acetic Acid ◽  
Carboxylic Acid ◽  
Hydrogen Bonds ◽  
Diabetic Neuropathy ◽  
Dihedral Angle ◽  
Phenyl Ring ◽  
Acid Moiety ◽  
Acta Cryst ◽  
Carboxylic Acid Groups

Epalerstat {systematic name: (5Z)-5-[(2E)-2-methyl-3-phenylprop-2-en-1-ylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidine-3-acetic acid} crystallized as an acetone monosolvate, C15H13NO3S2·C3H6O. In the epalerstat molecule, the methylpropylenediene moiety is inclined to the phenyl ring and the five-membered rhodamine ring by 21.4 (4) and 4.7 (4)°, respectively. In addition, the acetic acid moiety is found to be almost normal to the rhodamine ring, making a dihedral angle of 85.1 (2)°. In the crystal, a pair of O—H...O hydrogen bonds between the carboxylic acid groups of epalerstat molecules form inversion dimers with an R 2 2(8) loop. The dimers are linked by pairs of C—H...O hydrogen bonds, enclosing R 2 2(20) loops, forming chains propagating along the [101] direction. In addition, the acetone molecules are linked to the chain by a C—H...O hydrogen bond. Epalerstat acetone monosolvate was found to be isotypic with epalerstat tertrahydrofuran solvate [Umeda et al. (2017). Acta Cryst. E73, 941–944].

scholarly journals Electronic origin of the dependence of hydrogen bond strengths on nearest-neighbor and next-nearest-neighbor hydrogen bonds in polyhedral water clusters (H2O)n, n = 8, 20 and 24

2016 ◽  
Vol 18 (29) ◽  
pp. 19746-19756 ◽  
Author(s):  
Suehiro Iwata ◽  
Dai Akase ◽  
Misako Aida ◽  
Sotiris S. Xantheas
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Nearest Neighbor ◽  
Water Clusters ◽  
Hydrogen Donor ◽  
Donor And Acceptor ◽  
Bond Strengths

Comparison of the sum of the characteristic factors for some of the typical hydrogen donor and acceptor pairs with the CT term/kJ mol−1 (the upper value) and the O⋯O distance/in cubic (H2O)8.

Theoretical Modeling of the N-H and N-D Stretching Bands of Hydrogen-Bonded 1-Methylthymine Crystal and Its Deuterated Form

2006 ◽  
Vol 2 (4) ◽  
pp. 205-219
Author(s):  
Marek Boczar ◽  
Łukasz Boda ◽  
Marek J. Wójcik
Keyword(s):  
Hydrogen Bonds ◽  
High Frequency ◽  
Molecular Crystals ◽  
Low Frequency ◽  
Unit Cell ◽  
Fermi Resonance ◽  
Bending Vibrations ◽  
Theoretical Simulation ◽  
Stretching Vibrations ◽  
Centrosymmetric Dimers

Theoretical model for vibrational interactions in the hydrogen bonds in molecular crystals with four molecules forming two centrosymmetric dimers in the unit cell is presented. The model takes into account anharmonic-type couplings between the high-frequency N-H(D) and the low-frequency N•••O stretching vibrations in each hydrogen bond, resonance interactions (Davydov coupling) between equivalent hydrogen bonds in each dimer, resonance interdimer interactions within an unit cell and Fermi resonance between the N-H(D) stretching fundamental and the first overtone of the N-H(D) in-plane bending vibrations. The vibrational Hamiltonian, selection rules, and expressions for the integral properties of an absorption spectrum are derived. The model is used for theoretical simulation of the νs stretching bands of 1-methylthymine and its ND derivative at 300 K. The effect of deuteration is successfully reproduced by our model.

STRUCTURAL IMPLICATIONS OF O—H⋯O HYDROGEN BONDS IN INORGANIC CRYSTALS

2009 ◽  
Vol 23 (31n32) ◽  
pp. 3951-3958 ◽  
Author(s):  
FANGFANG ZHANG ◽  
DONGFENG XUE
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Spatial Frequency ◽  
Frequency Distribution ◽  
Structural Characteristics ◽  
Scatter Plot ◽  
Inorganic Crystal ◽  
Inorganic Crystals ◽  
Bond Strengths ◽  
Crystal Design

Structural characteristics of O — H ⋯ O hydrogen bonds in inorganic crystals were comprehensively investigated on the basis of a database study. It is shown that the multi-furcated hydrogen bonds are very common, therefore, the structures of hydrogen bonds in inorganic crystals are extremely flexible. The direction and distance preferences of hydrogen bonds were systematically analyzed through frequency distribution histograms and normalized spatial frequency distribution scatter plot. In addition, new bond valence parameters were proposed for O — H ⋯ O bonds in inorganic crystals fully taking into account the multi-furcated hydrogen bonds, which can be used to properly evaluate hydrogen bond strengths in inorganic crystals. The current work sheds some light on the usage of hydrogen bonds in inorganic crystal design.

scholarly journals The crystal structure, Hirshfeld surface analysis and energy frameworks of 2-[2-(methoxycarbonyl)-3,6-bis(methoxymethoxy)phenyl]acetic acid

2020 ◽  
Vol 76 (7) ◽  
pp. 1101-1106
Author(s):  
Mustapha Tiouabi ◽  
Raphaël Tabacchi ◽  
Helen Stoeckli-Evans
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Acetic Acid ◽  
Hydrogen Bonds ◽  
Title Compound ◽  
Hirshfeld Surface ◽  
Supramolecular Framework ◽  
Phenyl Acetic Acid ◽  
Oh Groups ◽  
Compound C

In the title compound, C14H18O8, (I), the methoxycarbonyl [–C(=O)OCH3] and the acetic acid [–CH2C(=O)OH] groups are inclined to the benzene ring by 79.24 (11) and 76.71 (13)°, respectively, and are normal to each other with a dihedral angle of 90.00 (13)°. In the crystal, molecules are linked by a pair of O—H...O hydrogen bonds forming the familiar acetic acid inversion dimer. The dimers are linked by two C—H...O hydrogen bonds and an offset π–π interaction [intercentroid distance = 3.6405 (14) Å], forming layers lying parallel to the (10\overline{1}) plane. The layers are linked by a third C—H...O hydrogen bond and a C—H...π interaction to form a supramolecular framework.

PCILO study of hydrogen bond and proton transfer in systems 1-methylthymine-acetamide and 1-methylthymine-acetic acid

1981 ◽  
Vol 46 (4) ◽  
pp. 957-962 ◽  
Author(s):  
Milan Remko
Keyword(s):  
Hydrogen Bond ◽  
Acetic Acid ◽  
Hydrogen Bonds ◽  
Proton Transfer ◽  
Quantum Chemical ◽  
Potential Functions ◽  
Double Proton Transfer ◽  
Proton Potential ◽  
Pcilo Method

Complexes containing two hydrogen bonds of the systems 1-methylthymine-acetamide and 1-methylthymine-acetic acid have been studied by the quantum-chemical PCILO method. In accordance with experiment our PCILO calculations have shown that acetic acid forms stronger hydrogen bonds than acetamide with 1-methylthymine. Further the PCILO method has been used to study of double proton transfer in O-H...O and N-H...O bonds of the complexes 1-methylthymine-acetamide and 1-methylthymine-acetic acid. Using equilibrium O...O and N...O distances, the PCILO calculations have given one-minimum proton potential functions. The proton transfer has not been observed. At somewhat longer N...O and O...O distances (0.30 nm) the PCILO calculations indicate a second minimum as a shoulder.

2-(3-Methyl-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-4-yl)acetic acid

2007 ◽  
Vol 63 (11) ◽  
pp. o4378-o4378 ◽  
Author(s):  
Rafal Kruszynski ◽  
Agata Trzesowska ◽  
Magdalena Przybycin ◽  
Kamil Gil ◽  
Maria Dobosz
Keyword(s):  
Hydrogen Bond ◽  
Acetic Acid ◽  
Hydrogen Bonds ◽  
Title Compound ◽  
Three Dimensional ◽  
Acid Group ◽  
Interatomic Distances ◽  
Compound C

All interatomic distances in the title compound, C5H7N3O2S, are normal. The 1,2,4-triazoline ring is planar and it is inclined at 78.61 (7)° to the planar acetic acid group. The molecules of the title compound are connected via O—H...N hydrogen bonds into zigzag chains along the [101] direction and by N—H...S hydrogen bonds into a three-dimensional net. In addition, a weak C—H...O hydrogen bond can also be found in the structure.

scholarly journals 2,2′,2′′,2′′′-(1,4-Phenylenedinitrilo)tetraacetic acid dihydrate

2012 ◽  
Vol 68 (6) ◽  
pp. o1623-o1623
Author(s):  
Juanzhi Yan ◽  
Ling Ma ◽  
Miaoli Zhu ◽  
Xiangdong Zhang ◽  
Chunhua Ge
Keyword(s):  
Hydrogen Bond ◽  
Acetic Acid ◽  
Hydrogen Bonds ◽  
Organic Molecule ◽  
Organic Molecules ◽  
Dihedral Angles ◽  
Water Molecules ◽  
Inversion Symmetry ◽  
Tetraacetic Acid ◽  
Compound C

In the title compound, C14H16N2O8·2H2O, the complete organic molecule is generated by crystallographic inversion symmetry. The dihedral angles between the aniline ring and the acetic acid groups are almost identical, viz. 82.61 (7) and 80.33 (7)°. In the crystal, O—H...O hydrogen bonds link the organic molecules and water molecules, forming zigzag chains the c axis. An intramolecular O—H...O hydrogen bond is also observed.

Past Results and Future Prospects of the Far-Infrared Studies of Hydrogen Bonding

1968 ◽  
Vol 22 (6) ◽  
pp. 641-649 ◽  
Author(s):  
R. J. Jakobsen ◽  
J. W. Brasch ◽  
Y. Mikawa
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Low Frequency ◽  
Far Infrared ◽  
Future Prospects ◽  
The Past ◽  
Ir Studies ◽  
Infrared Studies ◽  
Order Of Magnitude

In the past five years the number of papers concerned with far-ir studies of hydrogen bonding has increased by an order of magnitude. The results of some of these papers are presented in this review. Most of this work is concerned with the assignment of low frequency hydrogen bond vibrations. Since the major problem is reliable assignments, we discuss techniques used in making the assignments and emphasize the past work in which attempts have been made to substantiate those assignments. These assignments are discussed in terms of the different hydrogen bond vibrations associated with various types of hydrogen bonds. The main needs for future far ir hydrogen bond studies are listed.

Chlorine content and crystal chemistry of dellaite from the Birkhin gabbro massif, Eastern Siberia, Russia

2011 ◽  
Vol 75 (2) ◽  
pp. 379-394 ◽  
Author(s):  
T. Armbruster ◽  
B. Lazic ◽  
F. Gfeller ◽  
E. V. Galuskin ◽  
I. O. Galuskina ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Raman Spectroscopy ◽  
Chemical Composition ◽  
Hydrogen Bonds ◽  
Low Frequency ◽  
Structural Data ◽  
Eastern Siberia ◽  
X Ray ◽  
Cell Dimensions ◽  
Modular Structures

AbstractDellaite crystals of close to end-member composition, Ca6(Si2O7)(SiO4)(OH)2, and with ∼1.5 wt.% Cl. yielding Ca6(Si2O7)(SiO4)(OH)1.75Cl0.25 have been found in skarns within the gabbroid rocks of the Birkhin complex (Eastern Siberia, Russia). The greatest Cl content analysed in a dellaite domain in this skarn is 5.2 wt.% Cl corresponding to 0.8 Cl p.f.u. Dellaite occurs in altered merwmite-larnite-bredigite-gehlenite skarns and also in calcio-olivine skarns with residual larnite. The crystal structures of Cl-free and Cl-bearing (∼1.5 wt.% Cl) dellaite have been refined, including hydrogen positions, from single-crystal X-ray data to R1 = 3.7 and 3.8%, respectively. In addition, both dellaite varieties were studied by Raman spectroscopy indicating stronger hydrogen bonds for the Cl-bearing sample, which agrees with the structural data. Cl is strongly selective and enriches at one (O6) of the two OH positions allowing for the formation of a stronger hydrogen bond O8—H8…C16 compared to O8—H8…O6. Raman spectra of the domain with ∼0.8 Cl p.f.u. confirm the general enhancement of a low-frequency band in the OH range suggesting the dominance of the O—H…Cl hydrogen bond systems.Dellaite and killalaite, Ca3.2(H0.6Si2O7)(OH), have related modular structures, differentiated only by the Si2O7 units in killalaite and alternating Si2O7 and SiO4 units in dellaite. The similarity in cell dimensions and chemical composition suggests that trabzonite, Ca4Si3Oi0-2H2O, with Si3Oi0 trimers also belongs to the same family of structures.

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