A comparison of the C‒H bond dissociation enthalpies of sulfur-containing fused heterocyclic compounds to the C‒H bond dissociation enthalpies in other heterocycles

References

• Liu SQ, Brown CW, Berlin KD, Dhar A, Guruswamy S, Brown D, Gardner GJ, Birrer MJ, Benbrook DM. Synthesis of flexible sulfur-containing heteroarotinoids that induce apoptosis and reactive oxygen species with discrimination between malignant and benign cells. J Med Chem. 2004;47:999–1007. doi: 10.1021/jm030346v
   PubMed Web of Science ®Google Scholar
• Nosova EV, Lipunova GN, Charushin VN, Chupakhin ON. Fluorinated azines and benzazines containing oxygen or sulfur atoms. J Fluorine Chem. 2010;131:1267–1288. doi: 10.1016/j.jfluchem.2010.09.007
   Web of Science ®Google Scholar
• Messaoudi S, Brion J-D, Alami M. Transition-metal-catalyzed direct C‒H alkenylation, alkynylation, benzylation, and alkylation of (hetero)arenes. Eur J Org Chem. 2010;2010:6495–6516. doi: 10.1002/ejoc.201000928
   Web of Science ®Google Scholar
• Tang DTD, Collins KD, Glorius F. Completely regioselective direct C‒H functionalization of benzo[b]thiophenes using a simple heterogeneous catalyst. J Am Chem Soc. 2013;135:7450–7453. doi: 10.1021/ja403130g
   PubMed Web of Science ®Google Scholar
• Liger F, Pellet-Rostaing S, Popowycz F, Lemaire M. Bromination of 3-substituted benzo[b]thiophenes: access to raloxifen intermediate. Tetrahedron Lett. 2011;52:3736–3739. doi: 10.1016/j.tetlet.2011.05.043
   Web of Science ®Google Scholar
• Cho CH, Neuenswander B, Larock RC. Diverse methyl sulfone-containing benzo[b]thiophene library via iodocyclization and palladium-catalyzed coupling. J Comb Chem. 2010;12:278–285. doi: 10.1021/cc900172u
   PubMed Web of Science ®Google Scholar
• Inomata H, Toh A, Mitsui T, Fukuzawa SI. N-heterocyclic carbene copper(I) complex-catalyzed direct C‒H thiolation of benzothiazoles. Tetrahedron Lett. 2013;54:4729–4731. doi: 10.1016/j.tetlet.2013.06.104
   Web of Science ®Google Scholar
• Feng Y, Liu L, Wang JT, Huang H, Guo QX. Assessment of experimental bond dissociation energies using composite ab initio methods and evaluation of the performances of density functional methods in the calculation of bond dissociation energies. J Chem Inf Comput Sci. 2003;43:2005–2013. doi: 10.1021/ci034033k
   PubMedGoogle Scholar
• Feng Y, Liu L, Wang JT, Zhao SW, Guo QX. Homolytic C‒H and N–H bond dissociation energies of strained organic compounds. J Org Chem. 2004;69:3129–3138. doi: 10.1021/jo035306d
   PubMed Web of Science ®Google Scholar
• Zhao SW, Liu L, Fu Y, Guo QX. Assessment of the metabolic stability of the methyl groups in heterocyclic compounds using C‒H bond dissociation energies: effects of diverse aromatic groups on the stability of methyl radicals. J Phys Org Chem. 2005;18:353–367. doi: 10.1002/poc.856
   Web of Science ®Google Scholar
• Lu QQ, Yu HZ, Fu Y. Linear correlation between the C‒H activation barrier and the C–Cu/C‒H bond dissociation energy gap in Cu-promoted C‒H activation of heteroarenes. Chem Commun. 2013;49:10847–10849. doi: 10.1039/c3cc46069j
   PubMed Web of Science ®Google Scholar
• Auzmendi-Murua I, Charaya S, Bozzelli JW. Thermochemical properties of methyl-substituted cyclic alkyl ethers and radicals for oxiranes, oxetanes, and oxolanes: C‒H bond dissociation enthalpy trends with ring size and ether site. J Phys Chem A. 2013;117:378–392. doi: 10.1021/jp309775h
   PubMed Web of Science ®Google Scholar
• Wen Z, Li ZC, Shang ZF, Cheng JP. On the direction and magnitude of radical substituent effects:  the role of polar interaction on thermodynamic stabilities of benzylic C‒H bonds and related carbon radicals. J Org Chem. 2001;66:1466–1472. doi: 10.1021/jo001668z
   PubMed Web of Science ®Google Scholar
• Blanksby SJ, Ellison GB. Bond dissociation energies of organic molecules. Acc Chem Res. 2003;36:255–263. doi: 10.1021/ar020230d
   PubMed Web of Science ®Google Scholar
• Fu Y, Mou Y, Lin BL, Liu L, Guo QX. Structures of the X–Y–NO molecules and homolytic dissociation energies of the Y–NO bonds (Y‒C, N, O, S). J Phys Chem A. 2002;106:12386–12392. doi: 10.1021/jp0217029
   Web of Science ®Google Scholar
• Curtiss LA, Redfern PC, Raghavachari K. Gaussian-4 theory. J Chem Phys. 2007;126:084108–084120. doi: 10.1063/1.2436888
   PubMed Web of Science ®Google Scholar
• Montgomery JA, Frisch MJ, Ochterski JW, Petersson GA. A complete basis set model chemistry. VI. Use of density functional geometries and frequencies. J Chem Phys. 1999;110:2822–2827. doi: 10.1063/1.477924
   Web of Science ®Google Scholar
• Lee C, Yang W, Parr RG. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B. 1988;37:785–789. doi: 10.1103/PhysRevB.37.785
   PubMed Web of Science ®Google Scholar
• Zheng WR, Guo ZL, Chen ZC, Yang Q, Huang T. S‒O homolytic bond dissociation enthalpies in sulfoxides. Res Chem Intermed. 2012;38:1791–1806. doi: 10.1007/s11164-012-0503-3
   Web of Science ®Google Scholar
• Modelli A, Mussoni L, Fabbri D. Electron affinities of polycyclic aromatic hydrocarbons by means of B3LYP/6-31+G* calculations. J Phys Chem A. 2006;110:6482–6486. doi: 10.1021/jp0605911
   PubMed Web of Science ®Google Scholar
• Fu Y, Liu L, Yu H-Z, Wang Y-M, Guo Q-X. Quantum-chemical predictions of absolute standard redox potentials of diverse organic molecules and free radicals in acetonitrile. J Am Chem Soc. 2005;127:7227–7234. doi: 10.1021/ja0421856
   PubMed Web of Science ®Google Scholar
• Shi J, Huang X-Y, Wang J-P, Li R. A theoretical study on C–COOH homolytic bond dissociation enthalpies. J Phys Chem A. 2010;114:6263–6272. doi: 10.1021/jp910498y
   PubMed Web of Science ®Google Scholar
• Boese AD, Martin JML. Development of density functionals for thermochemical kinetics. J Chem Phys B. 2004;8:3405–3416. doi: 10.1063/1.1774975
   Web of Science ®Google Scholar
• Kang JK, Musgrave CB. Prediction of transition state barriers and enthalpies of reaction by a new hybrid density-functional approximation. J Chem Phys. 2001;115:11040–11051. doi: 10.1063/1.1415079
   Web of Science ®Google Scholar
• Benjamin JL, Patton LF, Maegan H, Donald GT. Adiabatic connection for kinetics. Phys Chem A. 2012;104:4812–4815.
   Google Scholar
• Hoe WM, Cohen AJ, Handy NC. Assessment of a new local exchange functional OPTX. Chem Phys Lett. 2001;341:319–328. doi: 10.1016/S0009-2614(01)00581-4
   Web of Science ®Google Scholar
• Perdew JP, Berke K, Ernzerhof M. Generalized gradient approximation made simple. Phys Rev Lett. 1996;77:3865–3868. doi: 10.1103/PhysRevLett.77.3865
   PubMed Web of Science ®Google Scholar
• Zhao Y, Lynch BJ, Truhlar, DG. Multi-coefficient extrapolated density functional theory for thermochemistry and thermochemical kinetics. Phys Chem Chem Phys. 2005;7:43–52. doi: 10.1039/b416937a
   Web of Science ®Google Scholar
• Zhao Y, Schultz NE, Truhlar DG. Exchange-correlation functional with broad accuracy for metallic and nonmetallic compounds, kinetics, and noncovalent interactions. J Chem Phys. 2005;123:161103–161106. doi: 10.1063/1.2126975
   PubMed Web of Science ®Google Scholar
• Zhao Y, Truhlar, DG. Hybrid meta density functional theory methods for thermochemistry, thermochemical kinetics, and noncovalent interactions:  the MPW1B95 and MPWB1 K models and comparative assessments for hydrogen bonding and van der Waals interactions. J Phys Chem A. 2004;108:6908–6918. doi: 10.1021/jp048147q
   Web of Science ®Google Scholar
• Zhao Y, Truhlar DG. Density functionals with broad applicability in chemistry. Acc Chem Res. 2008;41:157–167. doi: 10.1021/ar700111a
   PubMed Web of Science ®Google Scholar
• 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;125:194101–194118. doi: 10.1063/1.2370993
   PubMed Web of Science ®Google Scholar
• Dahlke EE, Truhlar DG. Improved density functionals for water. J Phys Chem B. 2005;109:15677–15683. doi: 10.1021/jp052436c
   PubMed Web of Science ®Google Scholar
• Chai JD, Head-Gordon M. Systematic optimization of long-range corrected hybrid density functionals. J Chem Phys. 2008;128:084106–084120. doi: 10.1063/1.2834918
   PubMed Web of Science ®Google Scholar
• Becke AD. Density-functional exchange-energy approximation with correct asymptotic behavior. Phys Rev A. 1988;38:3098–3100. doi: 10.1103/PhysRevA.38.3098
   PubMed Web of Science ®Google Scholar
• Lee C, Yang W, Parr RG. Development of the Colic-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B. 1988;37:785–789. doi: 10.1103/PhysRevB.37.785
   PubMed Web of Science ®Google Scholar
• Zhao Y, Truhlar DG. The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals. Theor Chem Acc. 2008;120:215–241. doi: 10.1007/s00214-007-0310-x
   Web of Science ®Google Scholar
• Reed AE, Curtiss LA, Weinhold F. Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint. Chem Rev. 1998;88:899–926. doi: 10.1021/cr00088a005
   Web of Science ®Google Scholar
• Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery Jr JA, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL , Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas Ö, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ. Gaussian 09, Revision. A.1. Wallingford, CT: Gaussian Inc.; 2009.
   Google Scholar
• Luo YR. Comprehensive handbook of chemical bond energies. Boca Raton, FL: CRC Press; 2007.
   Google Scholar
• Kruse H, Goerigk L, Grimme S. Why the standard B3LYP/6-31G* model chemistry should not be used in DFT calculations of molecular thermochemistry: understanding and correcting the problem. J Org Chem. 2012;77:10824–10834. doi: 10.1021/jo302156p
   PubMed Web of Science ®Google Scholar
• Sarish SP, Nembenna S, Nagendran S, Roesky HW. Chemistry of soluble β-diketiminatoalkaline-earth metal complexes with M–X bonds (M‒Mg, Ca, Sr; X‒OH, halides, H). Acc Chem Res. 2008;41:157–170. doi: 10.1021/ar700111a
   PubMed Web of Science ®Google Scholar
• Segovia ME, Irving K, Ventura ON. Density functional and chemical model study of the competition between methyl and hydrogen scission of propane and β-scission of the propyl radical. Theor Chem Acc. 2013;132:1301–1319. doi: 10.1007/s00214-012-1301-0
   Web of Science ®Google Scholar
• Chéron N, Ramozzi R, Kaïm LE, Grimaud L, Fleurat-Lessard P. Substituent effects in ugi-smiles reactions. J Phys Chem A. 2013;117:8035–8042. doi: 10.1021/jp4052227
   PubMed Web of Science ®Google Scholar
• Mbiya W, Chipinda I, Siegel PD, Mhike M, Simoyi RH. Substituent effects on the reactivity of benzoquinone derivatives with thiols. Chem Res Toxicol. 2013;26:112–123. doi: 10.1021/tx300417z
   PubMed Web of Science ®Google Scholar
• Menon AS, Henry DJ, Bally T, Radom L. Effect of substituents on the stabilities of multiply-substituted carbon-centered radicals. Org Biomol Chem. 2011;9:3636–3657. doi: 10.1039/c1ob05196b
   PubMed Web of Science ®Google Scholar
• Chattaraj PK, González-Rivas N, Matus MH, Galván M. Substituent effects. J Phys Chem A. 2005;109:5602–5607. doi: 10.1021/jp045319a
   PubMed Web of Science ®Google Scholar
• Mó O, Yáñez M, Elguero J, Roux MV, Jiménez P, Dávalos JZ, Ribeiro da Silva MAV, Maria das Dores MC, Ribeiro da Silva MDMC, Cabildo P, Claramunt R. Substituent effects on enthalpies of formation: benzene derivatives. J Phys Chem A. 2003;107:366–371. doi: 10.1021/jp0265790
   Web of Science ®Google Scholar
• Liu L, Fu Y, Liu R, Li R-Q, Guo Q-X. Hammett equation and generalized Pauling's electronegativity equation. J Chem Inf Comput Sci. 2004;44:652–657. doi: 10.1021/ci0342122
   PubMedGoogle Scholar
• Yu YY, Fu Y, Liu L, Guo QX. Theoretical study of remote substituent effects on X–H (X‒CH2, NH, O) bond dissociation energies of azulene. Chin J Chem. 2007;25:1014–1022. doi: 10.1002/cjoc.200790162
   Web of Science ®Google Scholar
• Zheng WR, Xu WX, Wang YX, Chen ZC. The theoretical assessment and prediction of C–Br bond dissociation enthalpies. Comput Theor Chem. 2014;1027:116–124. doi: 10.1016/j.comptc.2013.11.012
   Web of Science ®Google Scholar
• Song KS, Liu L, Guo QX. Effects of α-ammonium, α-phosphonium, and α-sulfonium groups on C‒H bond dissociation energies. J Org Chem. 2003;68:4604–4607. doi: 10.1021/jo020709j
   PubMed Web of Science ®Google Scholar