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Issue 7, 2018
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Reaction mechanism of hydrogen-tritium exchange reactions between several organic and HTO molecules: a role of the second HTO

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Abstract

The mechanism of hydrogen-tritium (H-T) exchange reactions between several small organic and HTO molecules have been investigated using M06-2X/6-311++G(d,p) method. The second HTO molecule is taken into account for both direct and addition–elimination H-T exchange reactions. The reactivity of small organic molecules for H-T exchange reactions is in the order of CH3COOH > CH3CH2OH > CH3CHO ≈ CH3COCH3 ≈ C2H4 and C3H6 > CH4, C2H6, and C3H8. In particular, the energies of activation in addition–elimination H-T exchange reactions of alkene with two HTO molecules become lower than those of direct H-T exchange ones. Our study reveals that (i) the reactivity of alkene with HTO molecules is comparable to that of aldehyde and ketone when the effect of the second HTO molecule is taken into account and (ii) the H-T exchange reactions between alkene and HTO molecules prefer addition–elimination H-T exchange mechanism, whereas other organic molecules favor a direct one.

Graphical abstract: Reaction mechanism of hydrogen-tritium exchange reactions between several organic and HTO molecules: a role of the second HTO

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Publication details

The article was received on 07 Dec 2017, accepted on 15 Jan 2018 and first published on 22 Jan 2018


Article type: Paper
DOI: 10.1039/C7RA13110K
Citation: RSC Adv., 2018,8, 3878-3888
  • Open access: Creative Commons BY license
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    Reaction mechanism of hydrogen-tritium exchange reactions between several organic and HTO molecules: a role of the second HTO

    T. Udagawa and M. Tachikawa, RSC Adv., 2018, 8, 3878
    DOI: 10.1039/C7RA13110K

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