The heats of formation of the haloacetylenes XCCY [X, Y = H, F, Cl]: basis set limit ab initio results and thermochemical analysis

References

• Smart , B. E. 1988 . Fluorine-containing Molecules: Structure, Reactivity, Synthesis. And Applications Edited by: Liebman , J. F. , Greenberg , A. and Dolbier , W. R. Jr . New York : VCH . See, for example, (a);(b) Slayden, S. W., Liebman, J. F., and Mallard, W. G., 1995, The Chemistry of Functional Groups, Supplement D2: The Chemistry of Organic Halides. Pseudohalides and Azides, edited by S. Patai and Z. Rappoport (Chichester: Wiley)
   Google Scholar
• Kütting , C. and Sander , W. 1999 . J. Am. chem. Soc. , 121 : 8891 See, for example, the use of difluoroacetylene as a precursor for (a) its isomer, difluorovinylidene:;(b) along with dichloroacetylene and the mixed chloro-fluoroacetylene, for their respective polymers: Gould, G. L., Eswara, V., Trifu, R. M., and Castner, D. G., 1999, J. Am. chem. Soc. 121, 3781
   Web of Science ®Google Scholar
• Chase , M. W. Jr . 1998 . NIST-JAN AF Thermochemical Tables, 4th Edn . J. phys. Chem. Ref. Data Monograph 8. ,
   Google Scholar
• Yamada , T. and Bozzelli , J. W. 1999 . J. phys. Chem. A , 103 : 7373
   Web of Science ®Google Scholar
• Berry , R. J. , Schwartz , M. and Marshall , P. 1998 . Computational Thermochemistry: Prediction and Estimation of Molecular Thermodynamics Edited by: Irikura , K. K. and Frurip , D. J. Washington, DC : American Chemical Society .
   Google Scholar
• Colegrove , B. T. and Thompson , T. B. 1997 . J. chem. Phys. , 106 : 1480
   Web of Science ®Google Scholar
• Rodriquez , C. F. , Bohme , D. K. and Hopkinson , A. C. 1993 . J. org. Chem. , 58 : 3344
   Web of Science ®Google Scholar
• Wiberg , K. B. and Rablen , P. R. 1993 . J. Am. Chem. Soc. , 115 : 9234
   Web of Science ®Google Scholar
• Deleeuw , B. J. , Fermann , J. T. , Xie , Y. and Schaefer , H. F. III . 1993 . J. Am. chem. Soc. , 115 : 1039
   Web of Science ®Google Scholar
• Coffey , D. Jr , Smith , B. J. and Radom , L. 1993 . J. chem. Phys. , 98 : 3952
   Web of Science ®Google Scholar
• Breidung , J. and Thiel , W. 2001 . J. molec. Spectrosc. , 205 : 28
   PubMed Web of Science ®Google Scholar
• Breidung , J. , Burger , H. , Kotting , C. , Kopitzky , R. , Sander , W. , Senzlober , M. , Thiel , W. and Willner , H. 1997 . Angew. Chem. Int. Ed. Engl. , 36 1983
   PubMed Web of Science ®Google Scholar
• Martin , J. M. L. and De Oliveira , G. 1999 . J. chem. Phys. , 111 : 1843
   Web of Science ®Google Scholar
• Martin , J. M. L. and Parthiban , S. 2001 . Quantum-mechanical Prediction of Thermochemical Data, Understanding Chemical Reactivity Edited by: Cioslowski , J. Vol. 22 , 31 – 65 . Dordrecht : Kluwer Academic Publishers .
   Google Scholar
• Raghavachari , K. , Trucks , G. W. , Pople , J. A. and Head-Gordon , M. 1989 . Chem. Phys. Lett. , 157 : 479
   Web of Science ®Google Scholar
• Parthiban , S. and Martin , J. M. L. 2001 . J. chem. Phys. , 114 : 6014
   Web of Science ®Google Scholar
• Purvis , G. D. III and Bartlett , R. J. 1982 . J. chem. Phys. , 76 1910
   Web of Science ®Google Scholar
• Werner , H.-J. , Knowles , P. J. , Almlöf , J. , Amos , R. D. , Berning , A. , Cooper , D. L. , Deegan , M. J. O. , Dobbyn , A. J. , Eckert , F. , Elbert , S. T. , Hampel , C. , Lindh , R. , Lloyd , A. W. , Meyer , W. , Nicklass , A. , Peterson , K. , Pitzer , R. , Stone , A. J. , Taylor , P. R. , Mura , M. E. , Pulay , P. , Schütz , M. , Stoll , H. and Thorsteinsson , T. Molpro is a package of ah initio programs
   Google Scholar
• Watts , J. D. , Gauss , J. and Bartlett , R. J. 1993 . J. chem. Phys. , 98 : 8718
   Web of Science ®Google Scholar
• Hampel , C. , Peterson , K. A. and Werner , H. J. 1992 . Chem. Phys. Lett. , 190 : 1
   Web of Science ®Google Scholar
• Becke , A. D. 1993 . J. chem. Phys. , 98 : 5648
   Web of Science ®Google Scholar
• Lee , C. , Yang , W. and Parr , R. G. 1988 . Phys. Rev. B , 37 : 785
   PubMed Web of Science ®Google Scholar
• Frisch , M. J. , Trucks , G. W. , Schlegel , H. B. , Scuseria , G. E. , Robb , M. A. , Cheeseman , J. R. , Zakrzewski , V. G. , Montgomery , J. A. , Stratmann , R. E. , Burant , J. C. , Dapprich , S. , Millam , J. M. , Daniels , A. D. , Kudin , K. N. , Strain , M. C. , Farkas , O. , Tomasi , J. , Barone , V. , Cossi , M. , Cammi , R. , Mennucci , B. , Pomelli , C. , Adamo , C. , Clifford , S. , Ochterski , J. , Petersson , G. A. , Ayala , P. Y. , Cui , Q. , Morokuma , K. , Malick , D. K. , Rabuck , A. D. , Raghavachari , K. , Foresman , J. B. , Cioslowski , J. , Ortiz , J. V. , Stefanow , B. B. , Liu , G. , Liashenko , A. , Piskorz , P. , Komaromi , I. , Gomperts , R. , Martin , R. L. , Fox , D. J. , Keith , T. , Al-Laham , M. A. , Peng , C. Y. , Nanayakkara , A. , Gonzalez , C. , Challacombe , M. , Gill , P. M. W. , Johnson , B. G. , Chen , W. , Wong , M. W. , Andres , J. L. , Head-Gordon , M. , Replogle , E. S. and Pople , J. A. 1998 . Gaussian 98, Revision A.3 Pittsburgh, PA : Gaussian, Inc. .
   Google Scholar
• Curtiss , L. A. , Raghavachari , K. , Trucks , G. W. and Pople , J. A. 1991 . J. chem. Phys. , 94 : 7221
   Web of Science ®Google Scholar
• Curtiss , L. A. , Raghavachari , K. , Redfern , P. C. , Rassolov , V. and Pople , J. A. 1998 . J. chem. Phys. , 109 : 7764
   Web of Science ®Google Scholar
• Montgomery , J. A. Jr , Frisch , M. J. , Ochterski , J. W. and Petersson , G. A. 1999 . J. chem. Phys. , 110 : 2822
   Web of Science ®Google Scholar
• Dunning , T. H. Jr , Peterson , K. A. and Woon , D. E. 1998 . Encyclopedia of Computational Chemistry Edited by: von Ragué Schleyer , P. Chichester : Wiley & Sons .
   Google Scholar
• Dunning , T. H. Jr . 1989 . J. chem. Phys. , 90 : 1007
   Web of Science ®Google Scholar
• Martin , J. M. L. and Uzan , O. 1998 . Chem. Phys. Lett. , 282 : 16
   Web of Science ®Google Scholar
• Feller , D. 1992 . J. chem. Phys. , 96 : 6104
   Web of Science ®Google Scholar
• Schwartz , C. 1963 . Methods in Computational Physics 2 Edited by: Alder , B. J. New York : Academic Press .
   Google Scholar
• Halkier , A. , Helgaker , T. , Jorgensen , P. , Klopper , W. , Koch , H. , Olsen , J. and Wilson , A. K. 1998 . Chem. Phys. Lett. , 286 : 243
   Web of Science ®Google Scholar
• Martin , J. M. L. and Taylor , P. R. 1994 . Chem. Phys. Lett. , 225 : 473
   Web of Science ®Google Scholar
• Martin , J. M. L. 1995 . Chem. Phys. Lett. , 242 : 343
   Web of Science ®Google Scholar
• Cowan , R. D. and Griffin , M. 1976 . J. opt. Soc. Am. , 66 : 1010
   Web of Science ®Google Scholar
• Martin , R. L. 1983 . J. phys. Chem. , 87 : 750
   Web of Science ®Google Scholar
• Gdanitz , R. J. and Ahlrichs , R. 1988 . Chem. Phys. Lett. , 143 : 413
   Web of Science ®Google Scholar
• Kendall , R. A. , Dunning , T. H. Jr and Harrison , R. J. 1992 . J. chem. Phys. , 96 : 6796
   Web of Science ®Google Scholar
• Afeefy , H. Y. , Liebman , J. F. and Stein , S. E. 2000 . NIST Chemistry WebBook. NIST Standard Reference Database Number 69 Edited by: Mallard , W. G. and Linstrom , P. J. Gaithersburg MD : National Institute of Standards and Technology . http://webbook.nist.gov.
   Google Scholar
• Martin , J. M. L. , Lee , T. J. and Taylor , P. R. 1998 . J. chem. Phys. , 108 : 676
   Web of Science ®Google Scholar
• Persson , B. J. , Taylor , P. R. and Martin , J. M. L. 1998 . J. phys. Chem. A , 102 : 2483
   Web of Science ®Google Scholar
• Breidung , J. , Hansen , T. and Thiel , W. 1996 . J. molec. Spectrosc. , 179 : 73
   Web of Science ®Google Scholar
• Breidung , J. and Thiel , W. 1997 . J. molec. Spectrosc. , 185 : 115
   PubMed Web of Science ®Google Scholar
• Breidung , J. , Bürger , H. , Senzlober , M. and Thiel , W. 1995 . Ber. Bunsenges. Phys. Chem. , 99 : 282
   Google Scholar
• Lias , S. G. , Karpas , Z. and Liebman , J. F. 1985 . J. Am. chem. Soc. , 107 : 6089
   Web of Science ®Google Scholar
• Fletcher , R. A. and Pilcher , G. 1971 . Trans. Faraday Soc. , 67 : 3191
   Google Scholar
• Lacher , J. R. , Emery , E. , Bohmfalk , E. and Park , J. D. 1956 . J. phys. Chem. , 60 : 492 (b) reanalysed by Cox, J. D., and Pilcher, G., 1970, Thermochemistry of Organic and Organometallic Compounds (New York: Academic Press), pp. 1–636
   Web of Science ®Google Scholar
• Pedley , J. B. , Naylor , R. D. and Kirby , S. P. 1986 . Thermochemical Data of Organic Compounds, , 2nd Edn New York : Chapman & Hall .
   Google Scholar
• Wiberg , K. B. 1968 . Tetrahedron , 24 : 1083
   Web of Science ®Google Scholar
• Reed , A. E. , Curtiss , L. A. and Weinhold , F. 1988 . Chem. Rev. , 88 : 899
   Web of Science ®Google Scholar
• Flitcroft , T. L. and Skinner , H. A. 1958 . Trans. Farad. Soc. , 54 : 57
   Google Scholar
• Conn , J. B. , Kistiakowsky , G. B. and Smith , E. A. 1939 . J. Am. chem. Soc. , 61 : 1868 There is a 355-298 K correction of 0.5 kcal mol−1 given by Cox and Pilcher [47 b]
   Google Scholar
• Rogers , D. W. , Dagdagan , O. A. and Allinger , N. L. 1979 . J. Am. chem. Soc. , 101 : 671 Our value is a consensus result from analysis of the series of such compounds contained therein
   Web of Science ®Google Scholar
• Davis , H. E. , Allinger , N. L. and Rogers , D. W. 1985 . J. org. Chem. , 50 : 3601 Our value is a consensus result from analysis of the series of such compounds contained therein
   Web of Science ®Google Scholar
• Martin , J. M. L. , Sundermann , A. , Fast , P. L. and Truhlar , D. G. 2000 . J. chem. Phys. , 113 : 1348
   Web of Science ®Google Scholar
• Gurvich , L. V. , Veyts , I. V. and Alcock , C. B. , eds. 1989 . Thermodynamic Properties of individual Substances Vol. 1 , Boca Raton, FL : CRC Press .
   Google Scholar
• Smith , D. W. 1998 . J. phys. Chem. A. , 102 : 7086
   Web of Science ®Google Scholar
• Luo , Y.-R. and Benson , S. W. 1997 . J. phys. Chem. A. , 101 : 3042
   Web of Science ®Google Scholar
• Schaffer , F. , Verevkin , S. P. , Rieger , H. J. , Beckhaus , H.-D. and Rüchardt , C. 1997 . Liebig Ann. , : 1338
   Google Scholar
• Slayden , S. W. and Liebman , J. F. 1997 . The Chemistry of Functional Groups, Supplement A3: The Chemistry of Doubly-Bonded Functional Groups. Edited by: Patai , S. Chichester : Wiley . See [47 b] and
   Google Scholar
• Lacher , J. R. , Amador , A. and Park , J. D. 1967 . Trans. Farad. Soc. , 63 : 1608
   Google Scholar
• Manion , J. L. 2001 . J. phys Chem. Ref: Data , in press
   Google Scholar
• Martin , J. M. L. and Taylor , P. R. 1999 . J. phys. Chem. A , 103 : 4427
   Web of Science ®Google Scholar
• Martin , J. M. L. 1999 . Chem. Phys. Lett. , 310 : 271
   Web of Science ®Google Scholar
• Curtiss , L. A. , Redfern , P. C. , Raghavachari , K. and Pople , J. A. 2001 . J. chem. Phys. , 114 : 108
   Web of Science ®Google Scholar