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1
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(a) Manion, J. A.; Mulder, P.; Louw, R. Environ. Sci. Technol. 1985, 19, 280-282.
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Environ. Sci. Technol.
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Manion, J.A.1
Mulder, P.2
Louw, R.3
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4
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0032550841
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(a) Brink, R. W.; Louw, R.; Mulder, P. Appl. Catal. B 1998, 16, 219-226.
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Appl. Catal. B
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Brink, R.W.1
Louw, R.2
Mulder, P.3
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5
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0038770828
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Ph.D. Thesis, Leiden University
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(b) Brink, R. W. Ph.D. Thesis, Leiden University, 1999.
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(1999)
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Brink, R.W.1
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6
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0033880749
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and references therein
-
Dorrestijn, E.; Laarhoven, L. J. J.; Arends, I. W. C. E.; Mulder P. J. Anal. Appl. Pyrolysis 2000, 54, 153-192 and references therein.
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(2000)
J. Anal. Appl. Pyrolysis
, vol.54
, pp. 153-192
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Dorrestijn, E.1
Laarhoven, L.J.J.2
Arends, I.W.C.E.3
Mulder, P.4
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7
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-
0033310441
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-
and references therein
-
Dorrestijn, E.; Kranenburg, M.; Poinsot, D.; Mulder, P. Holzforschung 1999, 53, 611-616 and references therein.
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(1999)
Holzforschung
, vol.53
, pp. 611-616
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Dorrestijn, E.1
Kranenburg, M.2
Poinsot, D.3
Mulder, P.4
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8
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0030768537
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-
and references therein
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Rüchardt, C.; Gerst, M.; Ebenhoch, J. Angew. Chem., Int. Ed. Engl. 1997, 36, 1406-1430 and references therein.
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Angew. Chem., Int. Ed. Engl.
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Rüchardt, C.1
Gerst, M.2
Ebenhoch, J.3
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9
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0035812793
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Mulder, P.; Hemmink, S.; De Heer, M. I.; Lupo, M.; Santoro, D.; Korth, H. G. J. Org. Chem. 2001, 66, 6611-6619. 103, 68, 4247-4257
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J. Org. Chem.
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Mulder, P.1
Hemmink, S.2
De Heer, M.I.3
Lupo, M.4
Santoro, D.5
Korth, H.G.6
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11
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0038432919
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Ph.D. Thesis, Leiden University
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(b) Arends, I. W. C. E. Ph.D. Thesis, Leiden University, 1993.
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(1993)
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Arends, I.W.C.E.1
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12
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0000572061
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McMillen, D. F.; Ogier, W. C.; Ross, D. S. J. Org. Chem. 1981, 46, 3322-3326.
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(1981)
J. Org. Chem.
, vol.46
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McMillen, D.F.1
Ogier, W.C.2
Ross, D.S.3
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13
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0001458403
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(a) Manion, J. A.; McMillen, D. F.; Malhotra, M. Energy Fuels 1996, 10, 776-788.
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(1996)
Energy Fuels
, vol.10
, pp. 776-788
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Manion, J.A.1
McMillen, D.F.2
Malhotra, M.3
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14
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0001426491
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(b) However, the decarboxylation might also occur by an electrophilic pathway via protonation of the aromatic ring by another molecule of benzoic acid: Eskay. T. P.; Britt, P. F.; Buchanan, A. C., III Energy Fuels 1997, 11, 1278-1287.
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(1997)
Energy Fuels
, vol.11
, pp. 1278-1287
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Eskay, T.P.1
Britt, P.F.2
Buchanan A.C. III3
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15
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0038770829
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note
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(a) The most volatile of the investigated substrates is 4 (bp 448 K). Its vapor pressure at the applied temperature (630 K) is 4.9 atm (ref 10b). Charging the reaction tube with 0.6 mmol of 4, 2.2 mmol of 1 (bp 585 K), and 0.15 mmol of dibenzofuran (bp 560 K) (internal standard), leaves a headspace volume of 1.9 mL. Applying Raoult's law, approximately 30% of 4 would stay in the gas phase (decreasing to 14% with 6, bp 493 K). By addition of typically 0.6 mmol of water (only in the case of phenyl derivatives) - corresponding to approximately 19 atm of overpressure under ideal gas approximation - virtually the entire substrate remains in the liquid phase. The substrate/water ratio was at least 1. Water was chosen because of the obvious advantage of not adding additional organic material to the reaction mixture.
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17
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0035906075
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4: Angeloff, A.; Brunet, J.-J.; Legars, P.; Neibecker, D.; Souyri, D. Tetrahedron Lett. 2001, 42, 2301-2303.
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(2001)
Tetrahedron Lett.
, vol.42
, pp. 2301-2303
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Angeloff, A.1
Brunet, J.-J.2
Legars, P.3
Neibecker, D.4
Souyri, D.5
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19
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84986694135
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A comparable observation has been reported for the self-decomposition of 2-chloro-4-methoxy-1-naphthol. At room temperature and in the presence of an acid, this compound dimerizes within a few hours with loss of chloride and methoxyl into a mono-chloronaphthofuran derivative. Isomers with the Cl at the C-3 position are stable: Laatsch, H. Liebigs Ann. Chem. 1991, 385-386.
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(1991)
Liebigs Ann. Chem.
, pp. 385-386
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Laatsch, H.1
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20
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0038094122
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note
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fH(39) = 58.96.
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21
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0003363438
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Neutral thermochemical data
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Linstrom P. J., Mallard, W. G., Eds; July 2001; National Institute of Standards and Technology, Gaithersburg MD
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(b) Afeefy, H. Y.; Liebman, J. F.; Stein, S. E. Neutral Thermochemical Data. In NIST Chemistry WebBook, NIST Standard Reference Database Number 69; Linstrom P. J., Mallard, W. G., Eds; July 2001; National Institute of Standards and Technology, Gaithersburg MD, 2001 (http://webbook.nist.gov).
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(2001)
NIST Chemistry WebBook, NIST Standard Reference Database Number 69
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Afeefy, H.Y.1
Liebman, J.F.2
Stein, S.E.3
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23
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0003974166
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NIST Standard Reference Data; National Institute of Standards and Technology: Gaithersburg, MD
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(d) Stein, S. E.; Rukkers, J. M.; Brown, R. L. NIST Structures and Properties Database 25, version 2.0; NIST Standard Reference Data; National Institute of Standards and Technology: Gaithersburg, MD, 1994.
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(1994)
NIST Structures and Properties Database 25, Version 2.0
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Stein, S.E.1
Rukkers, J.M.2
Brown, R.L.3
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24
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0001628333
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(e) Shaw, R.; Golden, D. M.; Benson, S. W. J. Phys. Chem. 1977, 81, 1716-1729.
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(1977)
J. Phys. Chem.
, vol.81
, pp. 1716-1729
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Shaw, R.1
Golden, D.M.2
Benson, S.W.3
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25
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33845373648
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Shiner, C. S.; Vorndam, P. E.; Kass, S. R. J. Am. Chem. Soc. 1986, 108, 5699-5701.
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(1986)
J. Am. Chem. Soc.
, vol.108
, pp. 5699-5701
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Shiner, C.S.1
Vorndam, P.E.2
Kass, S.R.3
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27
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0000128449
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Mulder, P.; Saastad, O. W.; Griller, D. J. Am. Chem. Soc. 1988, 110, 4090-4092.
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(1988)
J. Am. Chem. Soc.
, vol.110
, pp. 4090-4092
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Mulder, P.1
Saastad, O.W.2
Griller, D.3
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28
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0037136807
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Korth, H.-G.; de Heer, M. I.; Mulder, P. J. Phys. Chem. A 2002, 106, 8779-8789.
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(2002)
J. Phys. Chem. A
, vol.106
, pp. 8779-8789
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Korth, H.-G.1
De Heer, M.I.2
Mulder, P.3
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29
-
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0038432921
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note
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rH of 2.40 (3a), -0.34 (3b), 0.70 (33a), -0.20 (33b), 0.64 (31b), 2.60 (10a), 0.40 (10b), 2.60 (35a), 0.90 (35b), and 2.10 (39b).
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-
-
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30
-
-
0038432922
-
-
note
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-1, respectively (data from ref 6, except for 1,3-cyclohexadiene, 1,4-cyclohexadiene). Thus DFT, for example, underestimates the BDE(C-H) in 1,4-cyclohexadiene and overestimates the HA for benzene suggesting an erroneous computational handling of the radical and the diene.
-
-
-
-
32
-
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0037756431
-
-
note
-
-1 below the best experimental value (ref 21e). As for the phenols, it may be assumed that the ABDE(N-H) values for the aromatic amines are sufficiently reliable (ref 21f). The change in BDE (O-H) or BDE(N-H) in phenyl derivatives upon ring substitution can be mainly attributed to the degree of delocalization of the unpaired electron in the corresponding phenoxyl and anilinyl radicals (refs 20c and 20f). This also appears to be valid when expanding the aromatic system from phenyl to anthracenyl. The effect is more profound for O-H than for N-H bonds, because of the higher intrinsic spin delocalization in aromatic oxyl than in aminyl radicals.
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-
-
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33
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0001586773
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(b) Wayner, D. D. M.; Lusztyk, E.; Pagé, D.; Ingold, K. U.; Mulder, P.; Laarhoven, L. J. J.; Aldrich, H. S. J. Am. Chem. Soc. 1995, 117, 8737-8744.
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(1995)
J. Am. Chem. Soc.
, vol.117
, pp. 8737-8744
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-
Wayner, D.D.M.1
Lusztyk, E.2
Pagé, D.3
Ingold, K.U.4
Mulder, P.5
Laarhoven, L.J.J.6
Aldrich, H.S.7
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34
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0034837520
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(c) Pratt, D. E.; De Heer, M. I.; Mulder, P.; Ingold, K. U. J. Am. Chem. Soc. 2001, 123, 5518-5526.
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(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 5518-5526
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Pratt, D.E.1
De Heer, M.I.2
Mulder, P.3
Ingold, K.U.4
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36
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0001650021
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(e) MacFaul, P. A.; Wayner, D. D. M.; Ingold, K. U. J. Org. Chem. 1997, 62, 3413-3414.
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(1997)
J. Org. Chem.
, vol.62
, pp. 3413-3414
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MacFaul, P.A.1
Wayner, D.D.M.2
Ingold, K.U.3
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37
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0037130675
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(f) Pratt, D. A.; Dilabio, G. A.; Valgimigli, L.; Pedulli, G. F.; Ingold, K. U. J. Am. Chem. Soc. 2002, 124, 11085-11092.
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(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 11085-11092
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Pratt, D.A.1
Dilabio, G.A.2
Valgimigli, L.3
Pedulli, G.F.4
Ingold, K.U.5
-
39
-
-
0034654215
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., DFT assigns a hydrogen bonded post transition-state complex as the lowest energy product instead of the two separated species: De Heer, M. I.; Mulder, P.; Korth, H.-G.; Ingold, K. U.; Lusztyk, J. J. Am. Chem. Soc. 2000, 122, 2355-2360.
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(2000)
J. Am. Chem. Soc.
, vol.122
, pp. 2355-2360
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-
De Heer, M.I.1
Mulder, P.2
Korth, H.-G.3
Ingold, K.U.4
Lusztyk, J.5
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40
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0003520123
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-
NIST Standard Reference Data, National Institute of Standards and Technology: Gaithersburg, MD
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Mallard, W. G.; Westley, F.; Herron, J. T.; Hampson, R. F.; Frizzell, D. H. NIST Chemical Kinetics Database, version 2Q98; NIST Standard Reference Data, National Institute of Standards and Technology: Gaithersburg, MD, 1998.
-
(1998)
NIST Chemical Kinetics Database, Version 2Q98
-
-
Mallard, W.G.1
Westley, F.2
Herron, J.T.3
Hampson, R.F.4
Frizzell, D.H.5
-
41
-
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0038094125
-
-
note
-
-1 the benzylic BDE(C-H) for 1, as computed by DFT (ref 20).
-
-
-
-
42
-
-
0038432923
-
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note
-
2CNH, and benzyl alcohol (after hydrogen abstraction from the solvent). Computations have revealed that the N-O bond in the adduct radical is weak, suggesting that the cleavage reaction is extremely fast.
-
-
-
-
43
-
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0038094124
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Manuscript in preparation
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(b) Sheeller, B.; Pratt, D. A.; Walton, J. C.; Korth, H.-G.; Mulder, P.; Ingold, K. U. Manuscript in preparation.
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-
-
Sheeller, B.1
Pratt, D.A.2
Walton, J.C.3
Korth, H.-G.4
Mulder, P.5
Ingold, K.U.6
-
44
-
-
0038094123
-
-
note
-
-1 at 630 K (ref 22).
-
-
-
-
45
-
-
0038094126
-
-
note
-
-14 (36) at 523 K were estimated.
-
-
-
-
46
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0032070955
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Such a reaction has been identified in the photoinduced polymerization of 4-chloroaniline: Hashimoto, Y.; Mafuné, F.; Kondow, T. J. Phys. Chem. B 1998, 102, 4295-4300.
-
(1998)
J. Phys. Chem. B
, vol.102
, pp. 4295-4300
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Hashimoto, Y.1
Mafuné, F.2
Kondow, T.3
-
47
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0038770831
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-
See ref 6, footnote 25
-
See ref 6, footnote 25.
-
-
-
-
48
-
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0037756433
-
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note
-
3 can be eliminated (through a 1,4-elimination through a six-centered transition state) leading to 20 directly.
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-
-
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49
-
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0038432925
-
-
note
-
DFT, rel (to 4-chloro-aniline, 13) is 3.5 for di(4-chlorophenyl)amine. These relative rates suggest that in experiments with 11 or 13 chlorophenylamines may be observed as reaction products, which is indeed the case, see Table 1 (footnote f).
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50
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0004133516
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Gaussian, Inc.: Pittsburgh, PA
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Gaussian 98, revision A.7; Gaussian, Inc.: Pittsburgh, PA, 1998.
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(1998)
Gaussian 98, Revision A.7
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