A comparative MP2 study between water- and acid-assisted proton transfer: allophanic acid as a case of study View Full Text


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Article Info

DATE

2016-10

AUTHORS

Abdol Reza Hajipour, Morteza Karimzadeh, Sirous Ghorbani, Hossein Farrokhpour, Alireza Najafi Chermahini

ABSTRACT

Electronic structures of allophanic acid were studied using MP2/6-311++G(d,p) level of theory. Five most stable tautomers were selected and stability of them was studied in detail. Obtained data showed that tautomer 1 having hydrogen atom in the central nitrogen N3 and also in a trans conformation of carbonyl and amino functional groups becomes the most stable one. Then, interconversion of these tautomers to each other was investigated step by step through internal rotation and proton transfer routes. Results indicated that movement of protons determines rate-determining step of all paths A–E. Effects of different solvents were carefully surveyed for each tautomer, and among investigated solvents, water made slight stabilization. Activation barrier for proton exchange assisted by one water molecule and one formic acid molecule was also studied, separately. Both molecules had a great influence on lowering barrier especially for proton transfer routes. Comparative MP2 study showed that the barrier will be lowered much more when acid-assisted proton exchange takes place. More... »

PAGES

1345-1362

References to SciGraph publications

  • 2016-06. MP2 study on the hydrogen-bonding interaction between 5-fluorocytosine and DNA bases: A, C, G, T in STRUCTURAL CHEMISTRY
  • 2014-01. Theoretical studies on proton transfer reaction of 3(5)-substituted pyrazoles in JOURNAL OF CHEMICAL SCIENCES
  • 2014-10. MP2 study on the hydrogen-bonding interaction between 5-fluorouracil and DNA bases: A,C,G,T in STRUCTURAL CHEMISTRY
  • 2012-06. Theoretical study on the hydrogen bonding of five-membered heteroaromatics with water in STRUCTURAL CHEMISTRY
  • 2015-02. Tautomerism and mechanism of intramolecular proton transfer under the gas phase and micro-hydrated solvent conditions: biuret as a case study in STRUCTURAL CHEMISTRY
  • 2014-08. Insight into the acidic behavior of oxazolidin-2-one, its thione and selone analogs through computational techniques in STRUCTURAL CHEMISTRY
  • 2014-06. MP2 study on the hydrogen-bonding interaction between O4-methylthymine and DNA bases: A, C, G, and T in STRUCTURAL CHEMISTRY
  • 2014-04. Impacts of medium, substituents, and specific interactions with water on hydration of carbonyl compounds in STRUCTURAL CHEMISTRY
  • 2011-02. Theoretical studies on tautomerism of tetrazole 5-thion in STRUCTURAL CHEMISTRY
  • 2008-01. Effect of thione—thiol tautomerism on the inhibition of lactoperoxidase by anti-thyroid drugs and their analogues in JOURNAL OF CHEMICAL SCIENCES
  • 2013-08. Theoretical studies on tautomerism of imidazole-2-selenone in STRUCTURAL CHEMISTRY
  • 2015-12. Theoretical investigation on binding process of allophanate to allophanate hydrolase in CHEMICAL RESEARCH IN CHINESE UNIVERSITIES
  • Identifiers

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    http://scigraph.springernature.com/pub.10.1007/s11224-016-0753-6

    DOI

    http://dx.doi.org/10.1007/s11224-016-0753-6

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