Quadruple bonding in C2 and analogous eight-valence electron species.

Nature Chemistry
Sason ShaikPhilippe C Hiberty

Abstract

Triple bonding is conventionally considered to be the limit for multiply bonded main group elements, despite higher metal-metal bond orders being frequently observed for transition metals and lanthanides/actinides. Here, using high-level theoretical methods, we show that C(2) and its isoelectronic molecules CN(+), BN and CB(-) (each having eight valence electrons) are bound by a quadruple bond. The bonding comprises not only one σ- and two π-bonds, but also one weak 'inverted' bond, which can be characterized by the interaction of electrons in two outwardly pointing sp hybrid orbitals. A simple way of assessing the energy of the fourth bond is proposed and is found to be ~12-17 kcal mol(-1) for the isoelectronic species studied, and thus stronger than a hydrogen bond. In contrast, the analogues of C(2) that contain higher-row elements, such as Si(2) and Ge(2), exhibit only double bonding.

References

Apr 28, 2005·Journal of the American Chemical Society·Matthias LeinGernot Frenking
Nov 8, 2005·Science·Gernot Frenking
Jan 19, 2006·Journal of the American Chemical Society·Yusuke SugiyamaNorihiro Tokitoh
Jan 28, 2006·The Journal of Chemical Physics·Stefan Grimme
Jun 1, 2006·Journal of the American Chemical Society·Clark R Landis, Frank Weinhold
Oct 18, 2006·The Journal of Chemical Physics·Amir Karton, Jan M L Martin
Nov 9, 2006·Journal of the American Chemical Society·Victoria KravchenkoYitzhak Apeloig
Jun 15, 2007·Journal of Computational Chemistry·Milan Oncák, Martin Srnec
Apr 12, 2008·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·K S Ojha, R Gopal
Jul 24, 2008·Chemical Society Reviews·Kai Brandhorst, Jörg Grunenberg
Dec 17, 2008·Angewandte Chemie·Wei WuPhilippe C Hiberty
Sep 22, 2009·Angewandte Chemie·Peter R SchreinerGrzegorz Mloston
Jun 25, 2010·Physical Chemistry Chemical Physics : PCCP·Sason Shaik
Jan 8, 2011·Inorganic Chemistry·Nozomi TakagiGernot Frenking
Sep 1, 2009·Nature Chemistry·Sason ShaikPhilippe C Hiberty
Jan 11, 2011·Journal of Chemical Theory and Computation·Peifeng SuPhilippe C Hiberty
Mar 9, 2010·Journal of Chemical Theory and Computation·Bing XuHenry F Schaefer
Feb 1, 1999·Angewandte Chemie·Miriam KarniHelmut Schwarz

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Citations

Mar 8, 2013·Inorganic Chemistry·Fernando RuipérezIvan Infante
Jan 14, 2014·Journal of Chemical Theory and Computation·Lu T Xu, Thom H Dunning
May 11, 2016·ACS Central Science·Tao ZengRoald Hoffmann
Aug 8, 2013·Journal of the American Chemical Society·Frédéric A Perras, David L Bryce
Jul 18, 2015·The Journal of Physical Chemistry. a·Olha KrechkivskaTimothy W Schmidt
Feb 26, 2016·The Journal of Physical Chemistry. a·Thom H DunningBeth A Lindquist
Nov 18, 2015·Journal of Chemical Theory and Computation·Katharina Boguslawski, Paul W Ayers
Apr 17, 2016·The Journal of Chemical Physics·O KrechkivskaT W Schmidt
Nov 18, 2015·Journal of Chemical Theory and Computation·Zhenhua ChenWei Wu
Sep 8, 2015·The Journal of Chemical Physics·Laimutis BytautasKlaus Ruedenberg
Apr 6, 2016·Journal of Chemical Theory and Computation·David Wilian Oliveira de Sousa, Marco Antonio Chaer Nascimento
Jan 31, 2017·The Journal of Physical Chemistry. a·Aaron C WestKlaus Ruedenberg
Jan 13, 2016·Chemistry : a European Journal·Markus Hermann, Gernot Frenking
Jan 30, 2016·Chemistry : a European Journal·Mario PirisJesus M Ugalde
Jan 9, 2016·Chemistry : a European Journal·Wenli Zou, Dieter Cremer
Jul 14, 2017·Physical Chemistry Chemical Physics : PCCP·Felipe FantuzziMarco A C Nascimento
Dec 16, 2017·Angewandte Chemie·Philippe C Hiberty, Benoît Braïda
Apr 11, 2018·Angewandte Chemie·Daisuke YoshidaKoichi Ohno
Apr 29, 2016·Physical Chemistry Chemical Physics : PCCP·Yu LiuTimothy W Schmidt
Oct 30, 2014·Chemical Society Reviews·Avital ShurkiShina Caroline Lynn Kamerlin
May 12, 2017·Physical Chemistry Chemical Physics : PCCP·Yue ChenShigeyoshi Sakaki
May 23, 2012·Nature Chemistry·Michelle Francl
Apr 15, 2018·Chemistry : a European Journal·Daniel Menéndez-CrespoÁngel Martín Pendás
May 2, 2018·Chemistry : a European Journal·Congjie ZhangYirong Mo
Feb 19, 2015·Journal of Computational Chemistry·Marcos MenéndezÁngel Martín Pendás
Feb 19, 2013·Chemistry : a European Journal·Jordi PoaterFrancesc Teixidor
Jan 31, 2013·Angewandte Chemie·Sason ShaikRoald Hoffmann
Aug 11, 2018·Physical Chemistry Chemical Physics : PCCP·A Martín Pendás, E Francisco
Aug 3, 2013·Dalton Transactions : an International Journal of Inorganic Chemistry·Chakkittakandiyil AnushaPattiyil Parameswaran
Feb 13, 2018·Philosophical Transactions. Series A, Mathematical, Physical, and Engineering Sciences·A J C Varandas, C M R Rocha
Sep 17, 2013·Chemistry : a European Journal·David J D Wilson, Jason L Dutton
Sep 20, 2019·Chemistry : a European Journal·Ashim Nandi, Sebastian Kozuch
Jul 28, 2012·Chemistry : a European Journal·Peter Schröter, Viktoria H Gessner
May 24, 2017·Scientific Reports·Szilárd SzalayÖrs Legeza
Jul 18, 2017·Chemistry : a European Journal·Peter B Karadakov, Josh Kirsopp
Oct 19, 2019·Nature Communications·Chaoxian ChiJun Li
Nov 16, 2019·Nature Communications·B A LawsR W Field
May 1, 2013·Angewandte Chemie·Gernot Frenking, Markus Hermann
Feb 23, 2012·Nature Chemistry·Jörg Grunenberg

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