Influence of intermolecular amide hydrogen bonding on the geometry, atomic charges, and spectral modes of acetanilide: An ab initio study

Binoy, J.; Prathima, N. B.; Krishna, C. Murali; Chidangil, Santhosh; Joe, I. Hubert; Jayakumar, V. S.

doi:10.1134/s1054660x06080147

Cited by 11 publications

(10 citation statements)

References 30 publications

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“…A slight increase of the dipole moment of the residues in the β‐sheet polypeptide, acting synergetically with the hydrogen bonds, can contribute to the energetic stabilization of the longer chains. In particular, hydrogen bonds formed between backbone carbonyl oxygen and amide protons play a critical role in determining the conformational status of peptide chains . The Amide A band arising due to the NH stretching vibrations is characteristic of its functional group.…”

Section: Vibrational Analysismentioning

confidence: 99%

Molecular structure and vibrational spectra of N‐acetylglycine oligomers and polyglycine I using DFT approach

et al. 2014

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We have determined the geometric, vibrational, and electronic properties of N-acetylglycine oligomers by performing density functional theory quantum chemical calculations. The normal mode analysis was performed and the potential energy distribution was calculated among the internal coordinates. The optically active vibrational modes of PGI have been determined by selecting the modes from the calculated results of the pentamer and the observed vibrational spectra of PGI have been explained. The molecular electrostatic potential surface of N-acetylglycine pentamer reveals the sites of electrophilic attack and also provides clues for the role of electrostatic interactions involved in the reactivity. Natural bond orbital analysis has been performed to understand the charge transfer and various hyperconjugative interactions in the molecular system. The electronic properties of the oligomers have been discussed by calculating the transitions with the help of time dependent density functional theory method. The global reactivity descriptors such as hardness, chemical potential, and electrophilicity index have also been calculated.

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Section: Vibrational Analysismentioning

confidence: 99%

Molecular structure and vibrational spectra of N‐acetylglycine oligomers and polyglycine I using DFT approach

et al. 2014

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“…The trans-AA has a C s symmetry structure in which all the heavy atoms are lying in the aromatic plane [71]. Binoy et al [72] have demonstrated that a decrease in the NZH and CvO bond orders and an increase in the CZN bond orders can be observed in the vibrational spectra because of donoracceptor interaction. On the other hand, the experimental and theoretical studies on AA have been reported by some groups [73,74].…”

Section: Introductionmentioning

confidence: 97%

Excited-state hydrogen-bonding dynamics oftrans-acetanilide in an aqueous environment: a theoretical study

Zhang

2012

Molecular Simulation

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In this work, the time-dependent density functional theory (TDDFT) method was carried out to study the hydrogen-bonding dynamics in both singlet and triplet excited states of trans-acetanilide (AA) -(H 2 O) complexes formed by trans-acetanilide in a water (H 2 O) solvent. The ground-state geometric structure optimisations were calculated by the density functional theory method, but the electronic excitation energies and corresponding oscillation strengths of the low-lying electronically excited states for isolated AA, H 2 O monomers and hydrogen-bonded AA(CO) -(H 2 O) 1 , AA(NH) -(H 2 O) 1 dimers as well as the dihydrogen-bonded AA -(H 2 O) 2 trimer were calculated by the TDDFT method. In our system, the intermolecular hydrogen bonds CvO· · ·HZO and NZH· · ·OZH can also be formed. From the TDDFT results, we depicted the changes of different hydrogen-bonded complexes in various electronic excited states. According to Zhao's rule on the relationship between the electronic spectral shift and excited-state hydrogen-bonding dynamics, hydrogen bond strengthening can bring the relative electronic spectra redshift, whereas hydrogen bond weakening can make the corresponding electronic spectra shift to blue. In addition, we also discussed the frontier molecular orbitals and the electron density transition.

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“…Amides are known to form intra as well inter-molecular hydrogen bonds. 18 The compounds we present here as diaCEST agents do not exhibit contrast as an individual entity due to very fast exchange of their labile protons but do so only when they form ‘intermolecular hydrogen bonding (interMHB for brevity)’ mediated molecular chains or sheets. The interMHB helps to bring the exchange rate down to a favorable slow to medium exchange regime.…”

Section: Introductionmentioning

confidence: 99%

Paracetamol and other acetanilide analogs as inter-molecular hydrogen bonding assisted diamagnetic CEST MRI contrast agents

2021

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Influence of intermolecular amide hydrogen bonding on the geometry, atomic charges, and spectral modes of acetanilide: An ab initio study

Cited by 11 publications

References 30 publications

Molecular structure and vibrational spectra of N‐acetylglycine oligomers and polyglycine I using DFT approach

Molecular structure and vibrational spectra of N‐acetylglycine oligomers and polyglycine I using DFT approach

Excited-state hydrogen-bonding dynamics oftrans-acetanilide in an aqueous environment: a theoretical study

Paracetamol and other acetanilide analogs as inter-molecular hydrogen bonding assisted diamagnetic CEST MRI contrast agents

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