83
Views
0
CrossRef citations to date
0
Altmetric
Original Research

Switching of carbene spin states: effect of hydrogen bond donors

, , &
Pages 1-6 | Published online: 20 Jul 2015

References

  • Kirmse W. Carbene Chemistry. New York, NY: Academic Press; 1971.
  • Jones M, Moss RA, editors. Carbenes. Vols 1 and 2. New York, NY: Wiley Interscience; 1973 and 1975.
  • Brinker UH, editor. Advanced in Carbene Chemistry. Vol 1. Greenwich, CT: JAI Press; 1994.
  • Brinker UH, editor. Advanced in Carbene Chemistry. Vol 2. Stamford, CT: JAI Press; 1998.
  • Brinker UH, editor. Advanced in Carbene Chemistry. Vol 3. Amsterdam: Elsevier; 2001.
  • Moss RA, Platz MS, Jones M Jr, editors. Reactive Intermediate Chemistry. Hoboken, NJ: Wiley-Interscience; 2004.
  • McKellar ARW, Bunker PR, Sears TJ, Evenson KM, Saykally RJ, Langhoff SR. Far infrared laser magnetic resonance of singlet methylene: Singlet–triplet perturbations, singlet–triplet transitions, and the singlet–triplet splitting. J Chem Phys. 1983;79(11):5251–5264.
  • Balasubramanian K, McLean AD. The singlet–triplet energy separation in silylene. J Chem Phys. 1986;85(9):5117–5119.
  • Allen WD, Schaefer HF. geometrical structures, force constants, and vibrational spectra of SiH, SiH2, SiH3, and SiH4. Chem Phys. 1986;108(2):243–274.
  • Baird NC, Taylor KF. Multiplicity of the ground state and magnitude of the T1-S0 gap in substituted carbenes. J Am Chem Soc. 1978;100(5):1333–1338.
  • Hirai K, Itoh T, Tomioka H. Persistent triplet carbenes. Chem Rev. 2009;109(8):3275–3332 and references therein.
  • Wang Y, Hadad CM, Toscano JP. Solvent dependence of the 2-naphthyl(carbomethoxy)carbene singlet−triplet energy gap. J Am Chem Soc. 2002;124(8):1761–1767.
  • Sitzman EV, Langan JG, Eisenthal KB. Intermolecular effects on intersystem crossing studied on the picosecond timescale: the solvent polarity effect on the rate of singlet-to-triplet intersystem crossing of diphenylcarbene. J Am Chem Soc. 1984;106(6):1868–1869.
  • Langan JG, Sitzmann EV, Eisenthal KB. Picosecond laser studies on the effect of structure and environment on intersystem crossing in aromatic carbenes. Chem Phys Lett. 1984;110(5):521–527.
  • Sitzmann V, Langan JG, Griller D, Eisenthal KB. Effects of solvent polarity and structure on intersystem crossing in diphenylcarbenes. A picosecond laser study on dimesitylcarbene. Chem Phys Lett. 1989;161(4–5):353–360.
  • Wang J, Kubicki J, Gustafson TL, Platz MS. The dynamics of carbene solvation: an ultrafast study of p-biphenylyltrifluoromethylcarbene. J Am Chem Soc. 2008;130(7):2304–2313.
  • Hadel LM, Platz MS, Scaiano JC. Study of hydrogen atom abstraction reactions of triplet diphenylcarbene in solution. J Am Chem Soc. 1984;106(2):283–287.
  • Kirmse W, Kilian J, Steenken S. Carbenes and the oxygen-hydrogen bond: spectroscopic evidence for protonation of diarylcarbenes to give diarylcarbenium ions. J Am Chem Soc. 1990;112(17):6399–6400.
  • Costa P, Sander W. Hydrogen bonding switches the spin state of diphenylcarbene from triplet to singlet. Angew Chem Int Ed. 2014;53(20):5122–5125.
  • Costa P, Olivia MF, Garcia ES, Sander W. The highly reactive benzhydryl cation isolated and stabilized in water ice. J Am Chem Soc. 2014;136(44):15625–15630.
  • Kirmse W. In: Brinker UH, editor. Advances in Carbene Chemistry.Vol 1. Greenwich, CT: JAI Press; 1994:1–57.
  • Kirmse W. In: Brinker UH, editor. Advances in Carbene Chemistry. Vol 3. Amsterdam: Elsevier Science BV; 2001:1–51.
  • Becke AD. Density-functional thermochemistry. III. The role of exact exchange. J Chem Phys. 1993;98(7):5648–5652.
  • Lee C, Yang W, Parr RG. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B Condens Matter. 1988;37(2):785–789.
  • Baer R, Neuhauser D. Density functional theory with correct long-range asymptotic behavior. Phys Rev Lett. 2005;94(4):043002.
  • Livshits E, Baer R. A well-tempered density functional theory of electrons in molecules. Phys Chem Chem Phys. 2007;9(23):2932–2941.
  • Livshits E, Baer R. A density functional theory for symmetric radical cations from bonding to dissociation. J Phys Chem A. 2008;112(50):12789–12791.
  • Grimme S, Antony J, Ehrlich S, Krieg H. A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu. J Chem Phys. 2010;132(15):154104–154119.
  • Iikura H, Tsuneda T, Yanai T, Hirao K. A long-range correction scheme for generalized-gradient-approximation exchange functionals. J Chem Phys. 2001;115(8):3540–3544.
  • Zhao Y, Truhlar DG. A new local density functional for main-group thermochemistry, transition metal bonding, thermochemical kinetics, and noncovalent interactions. J Chem Phys. 2006;125(19):194101–194118.
  • Pople JA, Head-Gordon M, Raghavachari K. Quadratic configuration interaction. A general technique for determining electron correlation energies. J Chem Phys. 1987;87(10):5968–5975.
  • Neese F. ORCA – An Ab Initio, Density Functional and Semiempirical Program Package (version 3.0.2). University of Bonn, 2008.
  • Valiev M, Bylaska EJ, Govind N, et al. NWChem: version 6.1: a comprehensive and scalable open-source solution for large scale molecular simulations. Comput Phys Commun. 2010;181(9):1477–1489.
  • Bader RFW. Atoms in Molecules: A Quantum Theory. Oxford, UK: Oxford University Press; 1990.
  • Silvi B, Savin A. Classification of chemical bonds based on topological analysis of electron localization functions. Nature. 1994;371(20):683–686.
  • Becke AD, Edgecombe KE. A simple measure of electron localization in atomic and molecular systems. J Chem Phys. 1990;92(9):5397–5403.
  • Tian L. Multiwfn: A Multifunctional Wavefunction Analyzer (version 3.1). Available from: http://Multiwfn.codeplex.com. Accessed May 22, 2015.
  • Sulzbach HM, Bolton E, Lenoir D, Schleyer PvR, Schaefer HF III. Tetra-tert-butylethylene: an elusive molecule with a highly twisted double bond. can it be made by carbene dimerization? J Am Chem Soc. 1996;118(41):9908–9914.
  • Richards CA Jr, Kim S-J, Yamaguchi Y, Schaefer HF III. Dimethylcarbene: a singlet ground state? J Am Chem Soc. 1995;117(40):10104–10107.
  • Huheey JE, Keiter EA, Keiter RL. Inorganic Chemistry: Principles of Structure and Reactivity, 4th ed. Singapore: Pearson Education Pte Ltd; 2004.