Density functional theory study of intermolecular interactions of cyclic tetrazole dimers

Chermahini, Alireza Najafi; Ghaedi, Aseyeh; Teimouri, Abbas; Momenbeik, Fariborz; Dabbagh, Hossein A.

doi:10.1016/j.theochem.2008.07.023

Cited by 17 publications

(12 citation statements)

References 29 publications

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“…This finding is in accordance with our previously reported finding in the study of substituent effect on hydrogen boning strength of cyclic tetrazole dimers [24]. The previously reported binding energy of cyclic and symmetrical dimer of acetic acid calculated at B3LYP/6-311G(d,p) level was reported as 15.85 kcal/mol [25].…”

Section: Energies Of Dimerssupporting

confidence: 93%

Ab initio and DFT studies of hydrogen bond interactions in difluoroacetic acid dimer

2010

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Density functional theory (DFT) and ab initio calculations were performed for difluoroacetic acid (DFA). Eight theoretically possible conformers were considered and by using conformational analysis only three stable conformers were found. The hydrogen bonding interaction of DFA complex has been investigated using DFT and ab initio methods for cis conformers. Stabilization energies of dimers including basis set superposition error and ZPE were found in the range 8.89-13.08 kcal mol -1 . It was found that EFC dimer is slightly more stable. Red shift of O-H bond in the range -226.3 to 505.7 cm -1 predicted for dimers. The natural bond orbital analysis was applied to characterize nature of the interaction.

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Section: Energies Of Dimerssupporting

confidence: 93%

Ab initio and DFT studies of hydrogen bond interactions in difluoroacetic acid dimer

2010

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“…In addition the tautomerism behavior and NMR spectra of 5-tetrazole thion were studied earlier [17]. In the continuum with our studies on tetrazole derivatives [18][19][20][21], herein we report results of our calculations on tautomerism of the tetrazole thion compound. In this study five tautomers have been subjected to ab initio and DFT type calculations.…”

Section: Introductionmentioning

confidence: 84%

Theoretical studies on tautomerism of tetrazole 5-thion

2010

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Detailed investigation of the tautomerism of all possible forms of tetrazole thion (A and E) and its tetrazole forms (B-D) induced by proton transfer in the gas phase, in a continuum solvent, and in a microhydrated environment with 1 explicit water molecule was carried out by calculations at MP2, QCISD, CBS-Q, CBS-QB3, and density functional theory (DFT). It was found that in the gas phase and solvent tetrazole thion (form A) is the most stable isomer. In addition variation of dipole moments was studied in the gas phase and in the solvent. Water molecule was gradually put in different regions in the vicinity of five isomers. It was found that water can forms different hydrogen bonding with molecule.Keywords Tetrazole thion Á Tautomersim Á Solvent effect Á Specific solvent effect Á Hydrogen bonding Á DFT Á MP2 Electronic supplementary material The online version of this article (

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“…H-Bonded Interactions of 1H-Tetrazoles and Tetrazolates in Crystal Structures in the CSD 16. Table gives mean H-bond geometryinvolving X = N/O acceptors and N/O−H donors in 1H-tetrazoles (N1−H), N1−Z-tetrazoles (Z = C, N, O, H) and in tetrazolates.…”

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The Hydrogen Bond Environments of 1H-Tetrazole and Tetrazolate Rings: The Structural Basis for Tetrazole–Carboxylic Acid Bioisosterism

Allen

Groom

Liebeschuetz

et al. 2012

J. Chem. Inf. Model.

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Bioisosterism involving replacement of a carboxylic acid substituent by 1H-tetrazole, yielding deprotonated carboxylate and tetrazolate under physiological conditions, is a well-known synthetic strategy in medicinal chemistry. To improve our overall understanding of bioisosterism, we have used this example to study the geometrical and energetic aspects of the functional group replacement. Specifically, we use crystal structure informatics and high-level ab initio calculations to study the hydrogen bond (H-bond) energy landscapes of the protonated and deprotonated bioisosteric pairs. Each pair exhibits very similar H-bond environments in crystal structures retrieved from the CSD, and the attractive energies of these H-bonds are also very similar. However, by comparison with -COOH and -COO(-), the H-bond environments around 1H-tetrazole and tetrazolate substituents extend further, by about 1.2 Å, from the core of the connected molecule. Analysis of pairs of PDB structures containing ligands which differ only in having a tetrazole or a carboxyl substituent and which are bound to the same protein indicates that the protein binding site must flex sufficiently to form strong H-bonds to either substituent. A survey of DrugBank shows a rather small number of tetrazole-containing drugs in the 'approved' and 'experimental' drug sections of that database.

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Density functional theory study of intermolecular interactions of cyclic tetrazole dimers

Cited by 17 publications

References 29 publications

Ab initio and DFT studies of hydrogen bond interactions in difluoroacetic acid dimer

Ab initio and DFT studies of hydrogen bond interactions in difluoroacetic acid dimer

Theoretical studies on tautomerism of tetrazole 5-thion

The Hydrogen Bond Environments of 1H-Tetrazole and Tetrazolate Rings: The Structural Basis for Tetrazole–Carboxylic Acid Bioisosterism

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