Theoretical study of extremely long yet stable carbon-carbon bonds

Effect of attractive C[[ampi]]pound;H interactions and small Radical Stabilization of Diamondoids

Daeheum Cho, Yasuhiro Ikabata, Takeshi Yoshikawa, Yong Lee Jin, Hiromi Nakai

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

The origin of the stability of diamondoid dimers containing very long carbon-carbon bonds was examined using density functional theory (DFT) calculations with local response dispersion correction. It has been suggested that noncovalent CH[[ampi]]pound;HC contacts are the probable source of their extraordinary stability as evidenced by dispersion-corrected DFT calculations. In this work, we numerically proved that the small radical stabilization energy, which was achieved through the geometric relaxation of cleaved radicals, led to the high stability of diamondoid dimers compared to other hydrocarbons. The bond energy density analysis showed that the CH[[ampi]]pound;HC contacts are repulsive though the dispersion force somewhat stabilizes the dimer. We further decomposed CH[[ampi]]pound;HC interaction energies to discover strong attractive interaction between Ca[[ampi]]die; [[ampi]]pound;Ha[[ampi]]die;+ intermonomer contacts.

Original languageEnglish
Pages (from-to)1636-1641
Number of pages6
JournalBulletin of the Chemical Society of Japan
Volume88
Issue number12
DOIs
Publication statusPublished - 2015

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Dimers
Carbon
Stabilization
Density functional theory
Hydrocarbons

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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title = "Theoretical study of extremely long yet stable carbon-carbon bonds: Effect of attractive C[[ampi]]pound;H interactions and small Radical Stabilization of Diamondoids",
abstract = "The origin of the stability of diamondoid dimers containing very long carbon-carbon bonds was examined using density functional theory (DFT) calculations with local response dispersion correction. It has been suggested that noncovalent CH[[ampi]]pound;HC contacts are the probable source of their extraordinary stability as evidenced by dispersion-corrected DFT calculations. In this work, we numerically proved that the small radical stabilization energy, which was achieved through the geometric relaxation of cleaved radicals, led to the high stability of diamondoid dimers compared to other hydrocarbons. The bond energy density analysis showed that the CH[[ampi]]pound;HC contacts are repulsive though the dispersion force somewhat stabilizes the dimer. We further decomposed CH[[ampi]]pound;HC interaction energies to discover strong attractive interaction between Ca[[ampi]]die; [[ampi]]pound;Ha[[ampi]]die;+ intermonomer contacts.",
author = "Daeheum Cho and Yasuhiro Ikabata and Takeshi Yoshikawa and Jin, {Yong Lee} and Hiromi Nakai",
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T2 - Effect of attractive C[[ampi]]pound;H interactions and small Radical Stabilization of Diamondoids

AU - Cho, Daeheum

AU - Ikabata, Yasuhiro

AU - Yoshikawa, Takeshi

AU - Jin, Yong Lee

AU - Nakai, Hiromi

PY - 2015

Y1 - 2015

N2 - The origin of the stability of diamondoid dimers containing very long carbon-carbon bonds was examined using density functional theory (DFT) calculations with local response dispersion correction. It has been suggested that noncovalent CH[[ampi]]pound;HC contacts are the probable source of their extraordinary stability as evidenced by dispersion-corrected DFT calculations. In this work, we numerically proved that the small radical stabilization energy, which was achieved through the geometric relaxation of cleaved radicals, led to the high stability of diamondoid dimers compared to other hydrocarbons. The bond energy density analysis showed that the CH[[ampi]]pound;HC contacts are repulsive though the dispersion force somewhat stabilizes the dimer. We further decomposed CH[[ampi]]pound;HC interaction energies to discover strong attractive interaction between Ca[[ampi]]die; [[ampi]]pound;Ha[[ampi]]die;+ intermonomer contacts.

AB - The origin of the stability of diamondoid dimers containing very long carbon-carbon bonds was examined using density functional theory (DFT) calculations with local response dispersion correction. It has been suggested that noncovalent CH[[ampi]]pound;HC contacts are the probable source of their extraordinary stability as evidenced by dispersion-corrected DFT calculations. In this work, we numerically proved that the small radical stabilization energy, which was achieved through the geometric relaxation of cleaved radicals, led to the high stability of diamondoid dimers compared to other hydrocarbons. The bond energy density analysis showed that the CH[[ampi]]pound;HC contacts are repulsive though the dispersion force somewhat stabilizes the dimer. We further decomposed CH[[ampi]]pound;HC interaction energies to discover strong attractive interaction between Ca[[ampi]]die; [[ampi]]pound;Ha[[ampi]]die;+ intermonomer contacts.

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