Gas phase surface-catalyzed HCl addition to vinylacetylene: motion along a catalytic surface. Experiment and theory

Tetrahedron

Volumn 64, Issue 40, 2008, Pages 9357-9367

  Mascavage, Linda M ^a   Zhang Plasket, Fan ^b,c   Sonnet, Philip E ^b   Dalton, David R ^b  

^a ARCADIA UNIVERSITY   (United States)

^b Temple University   (United States)

^c MERCK RESEARCH LABORATORIES   (United States)

Author keywords

Alkenes; Alkynes; Electrophilic addition; FTIR

Indexed keywords

ACETYLENE DERIVATIVE; CLOROFENE; SODIUM CHLORIDE; VINYLACETYLENE;

ADDITION LINE; ARTICLE; CATALYSIS; GAS; GAS CHROMATOGRAPHY; INFRARED SPECTROSCOPY; KINETICS; MATHEMATICAL COMPUTING; PRIORITY JOURNAL;

EID: 49549118915     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.07.081     Document Type: Article

References (89)

1. Reviews include:
2. Larock R.C., and Leong W.W. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis Vol. 4 (1991), Pergamon, New York, NY 269-327
3. Sergeev G.B., Smirnov V.V., and Rostovshchikova T.N. Usp. Khim. 52 (1983) 455
4. Schmid G.H. In: Patai S. (Ed). The Chemistry of the Carbon-Carbon Triple Bond (1978), Wiley-Interscience, New York, NY 175 Part 1
5. Schmid G.H. In: Patai S. (Ed). The Chemistry of Double-Bonded Functional Groups Vol. 2 (1989), Wiley-Interscience, New York, NY 679-731 Supplement A, Part 1
6. Stroh R. Methoden Org. Chem. (Houben-Weyl) 3 (1962) 812
7. de la Mare P.B.D., and Bolton R. Electrophilic Additions to Unsaturated Systems (1966), Elsevier, New York, NY pp 51-72
8. de la Mare P.B.D., and Bolton R. Electrophilic Additions to Unsaturated Systems. 2nd ed. (1982), Elsevier, New York, NY pp 63-80
9. Mascavage L.M., and Dalton D.R. Trends Org. Chem. 4 (1993) 303-333
10. In: Stang P.J., and Diederich F. (Eds). Modern Acetylene Chemistry (1995), VCH, New York, NY 10-11
11. The following list is incomplete. It is provided as representative only and inclusion of, or failure to list, a work should not be taken as significant.
12. March J. Advanced Organic Chemistry. Reactions, Mechanisms, and Structure. 4th ed. (1992), Wiley, New York, NY p 749
13. McMurry J. Organic Chemistry. 5th ed. (2000), Brooks/Cole, Pacific Grove, CA p 278
14. Morrison R.T., and Boyd R.N. Organic Chemistry. 6th ed. (1992), Prentice Hall, Englewood Cliffs, NJ p 435
15. Streitweiser A., Heathcock C.H., and Kosower E.M. Introduction to Organic Chemistry. 4th ed. (1992), Macmillan, New York, NY p 312
16. Pine S.H., Hendrickson J.B., Cram D.J., and Hammond G.S. Organic Chemistry. 4th ed. (1980), McGraw-Hill, New York, NY p 504
17. McMurry J. Organic Chemistry. 4th ed. (1996), Brooks/Cole, Pacific Grove, CA p 266
18. Melloni G., Modena G., and Tonellato U. Acc. Chem. Res. 14 (1981) 227
19. Carothers W.H., Berecht G.J., and Collins A.M. J. Am. Chem. Soc. 54 (1932) 4066
20. Carothers W.H., and Berecht G.J. J. Am. Chem. Soc. 55 (1933) 2807
21. Carothers, W.H.; Coffman, D.D. U.S. Patent, 1,950,441, 13 March 1934.
22. Dolgopol'skii I.M., Trenke Y.V., and Blyumenthal M.Kh. Zh. Obschei khimii 33 (1963) 773
23. Dubois J.E., and Garnier F. J. Chem. Soc., Chem. Commun. (1968) 241
24. Dubois J.E., and Rausse M.F. J. Org. Chem. 37 (1972) 1770
25. Cook D., Lupien Y., and Schneider W.G. Can. J. Chem. 34 (1956) 957
26. Kiesel Z., Fowler P.W., Legon A.C., Devanne D., and Dixneuf P. J. Chem. Phys. 93 (1990) 6249
27. Tang T.-H., and Cui Y.-P. Can. J. Chem. 74 (1996) 1162
28. Herrebout W.A., and van der Veken B.J. J. Mol. Struct. 642 (2002) 1
29. Haugh M.J., and Dalton D.R. J. Am. Chem. Soc. 97 (1975) 5674
30. Costello F., Dalton D.R., and Poole J.A. J. Phys. Chem. 90 (1986) 5352
31. Tierney J., Costello F., and Dalton D.R. J. Org. Chem. 51 (1986) 5191
32. Mascavage L.M., Chi H., La S., and Dalton D.R. J. Org. Chem. 56 (1991) 585
33. Mascavage L.M., Zhang F., and Dalton D.R. J. Org. Chem. 59 (1994) 5048
34. Although, as usual, a plot of concentration versus integrated peak area for any of the signals of the R or P branches in the HCl spectrum could have been used, the particular region chosen shows minimal changes in the integrated intensity as a function of unspecified interactions (and/or complexes, etc.). See, e.g.
35. George W.O., Lewis R., Hussain G., and Rees G.J. J. Mol. Struct. 189 (1988) 211
36. Chackerian Jr. C., Goorvitch D., and Giver L.P. J. Mol. Spectrosc. 113 (1985) 373
37. For most of these reactions vinylacetylene apparently disappears slightly faster than HCl. This may be due to its (undetected) thermal polymerization on the walls of the cells. Unlike the present conditions, in the temperature range 70-120 °C, at 3-30 atm, significant polymerization results:. Matnishyan A.A., Grigoryan S.G., and Pogosyan E.T. Arm. Khim. Zh. 34 (1981) 342
38. Mascavage L.M., and Dalton D.R. Tetrahedron Lett. (1991) 3461
39. Sumner A.L., Menke E.J., Dubowski Y., Newberg J.T., Penner R.M., Hemminger J.C., Wingen L.M., Brauers T., and Finlayson-Pitts B.J. Phys. Chem. Chem. Phys. 6 (2004) 604
40. Mollanen D.E., Levinger N.E., Spry D.B., and Fayer M.D. J. Am. Chem. Soc. 129 (2007) 14311
41. Pease E.N. J. Am. Chem. Soc. 45 (1923) 1196
42. Bond G.C., and Wells P.B. J. Catal. 4 (1965) 211
43. Hougen O.A., and Watson K.M. Ind. Eng. Chem. 35 (1943) 529
44. Yang K.H., and Hougen O.A. Chem. Eng. Prog. 46 (1950) 146
45. For an excellent discussion of general principles, see:. Laidler K. Chemical Kinetics. 3rd ed. (1987), Harper and Row, New York, NY p 229
46. Rettner C.T., and Auerbach D.J. Science 263 (1994) 365
47. Langmuir I. Trans. Faraday Soc. 17 (1921) 621
48. Hinshelwood C.N. Kinetics of Chemical Change in Gaseous Systems (1926), Clarendon, Oxford p 145
49. Rideal E.K. Proc. Cambridge Philos. Soc. 35 (1939) 130
50. Rideal E.K. Chem. Ind. 62 (1943) 235
51. Eley D.D., and Rideal E.K. Proc. R. Soc. London, A 178 (1941) 429
52. Langmuir I. J. Am. Chem. Soc. 38 (1916) 2221
53. Langmuir I. J. Am. Chem. Soc. 40 (1918) 1361
54. Butt J.B. Reaction Kinetics and Reactor Design (1980), Prentice Hall, Englewood Cliffs, NJ p 167
55. Hill Jr. C.J. An Introduction to Chemical Engineering Kinetics and Reactor Design (1977), Wiley, New York, NY p 192
56. Whipple E.B., Stewart W.E., Reddy G.S., and Goldstein J.H. J. Chem. Phys. 34 (1961) 2136
57. Borg A., Smith Z., Gundersen G., and Klaeboe P. Spectrochim. Acta 36A (1980) 119
58. Ewing D.F., and Parry K.A. J. Chem. Soc. B (1970) 970
59. Jackman L.M., and Wiley R.H. J. Chem. Soc. (1960) 2881
60. Whipple E.B., Goldstein J.H., and Mandell L. J. Am. Chem. Soc. 82 (1960) 3010
61. Ronayne J., and Williams D.H. J. Chem. Soc. C (1967) 2642
62. Hirst R.C., and Grant D.M. J. Am. Chem. Soc. 84 (1962) 2009
63. Zhang, F. M.S. Thesis, Temple University, 1996.
64. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery Jr. J.A., Vreven T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J.E., Hratchian H.P., Cross J.B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador P., Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Gonzalez C., and Pople J.A. Gaussian 03, Revision C.02 (2004), Gaussian, Inc., Wallingford, CT
65. Becke A.D. J. Chem. Phys. 98 (1993) 5648
66. Lee C., Yang W., and Parr R.G. Phys. Rev. B 37 (1998) 785
67. Frisch M.J., Head-Gordon M., and Pople J.A. Chem. Phys. Lett. 166 (1990) 275 281
68. Ayala P.A., and Schlegel H.B. J. Chem. Phys. 107 (1997) 375
69. In the absence of detailed knowledge of the configuration of hydroxyl groups on the surface and because the modeling is appropriate only for the gas phase, water was specifically utilized in the computation. Since only one of the two protons is required for transfer during the addition reaction, it is presumed that any suitable surface-associated protruding -OH group would suffice.
70. Eigen M. Discuss. Faraday Soc. 39 (1965) 7
71. Bell R.P., and Horne D.G. J. Chem. Soc., Perkin Trans. 2 (1972) 1371
72. Williams I.H., Spangler D., Femec D.A., and Maggiora D.M. J. Am. Chem. Soc. 105 (1983) 31
73. Wiliams I.H. J. Am. Chem. Soc. 109 (1987) 6299
74. Yang W., and Grueckhammer D.G. J. Am. Chem. Soc. 123 (2001) 11004
75. Ilieva S., Galabov B., Musaev D.G., Morokuma K., and Schaeffer III H.F. J. Org. Chem. 68 (2003) 1496
76. Custer T.G., Kato S., Bierbaum V.M., Howard C.J., and Morrison G.C. J. Am. Chem. Soc. 126 (2004) 2744
77. Thornton E.R. J. Am. Chem. Soc. 89 (1967) 2915
78. More O'Ferrall R.A. J. Chem. Soc. B (1970) 274
79. Jencks W.P. J. Am. Chem. Soc. 72 (1972) 705
80. Kang Y., Skilles J.A., and Wightman J.P. J. Phys. Chem. 84 (1980) 1448
81. Verkruijsse H.D., and Brandsma L. Synth. Commun. 20 (1990) 3355
82. 2, potassium hydroxide must be protected from air once opened.
83. Kowalewski J., Granberg M., Karlsson F., and Vestin R. J. Magn. Reson. 21 (1976) 331
84. Tørneng E., Nielsen C.J., Klaeboe P., Hopf H., and Priebe H. Spectrochim. Acta 36A (1980) 975
85. Thompson H.W., and Torkington P. Proc. R. Soc. London, Ser. A 184 (1943) 21
86. Ferguson R.C. J. Phys. Chem. 68 (1964) 1594
87. Compton D.A.C., George W.O., Goodfield J.E., and Maddams W.F. Spectrochim. Acta 37A (1981) 147
88. Muskat I.E., and Northrup H.E. J. Am. Chem. Soc. 52 (1930) 4043
89. Jacobs T.L., Petty W.L., and Teach E.G. J. Am. Chem. Soc. 82 (1960) 4094