R.M. Pinto et al. / Journal of Molecular Structure 980 (2010) 163–171
171
Table 8
Experimental (VIE) and calculated (ꢀꢀ
i
) ionization energies (eV) of ortho-methylbenzyl azide, metha-methylbenzyl azide and para-methylbenzyl azide.
experimental energy uncertainty and molecular orbital, respectively.
D
E and MO stands for
Band
2-MBA
3-MBA
4-MBA
Experimental
VIE
Calc.
Experimental
VIE
Calc.
Experimental
VIE
Calc.
D
E
ꢀ
ꢀ
i
D
E
ꢀ
ꢀ
i
D
E
ꢀ
ꢀ
i
MO
a
b
c
d
e
9.03
9.47
10.88
11.84
13.36
0.02
0.04
0.01
0.08
0.13
9.09
9.20
10.30
11.98
13.42
9.02
9.61
10.88
11.69
13.16
0.01
0.01
0.01
0.02
0.02
8.99
9.31
8.89
9.50
10.88
11.66
13.14
0.01
0.01
0.01
0.02
0.03
8.95
9.36
HOMO
38
37
36
35
34
33
32
10.30
11.98
13.41
13.45
13.82
14.83
10.28
11.96
13.41
13.47
13.74
14.79
1
3.47
f
g
13.72
14.71
0.09
0.05
13.76
15.04
13.87
14.75
0.02
0.01
14.08
14.69
0.02
0.04
[
[
19] F. Martins, M.F. Duarte, M.T. Fernandez, G.J. Langley, P. Rodrigues, M.T. Barros,
M.L. Costa, Rapid Commun. Mass Spectrom. 18 (2004) 363–366.
20] M. Barros, M. Beyer, M. Costa, M. Duarte, M. Fernandez, F. Martins, P.
Rodrigues, P. Watts, Int. J. Mass Spectrom. 237 (2004) 65–73.
Acknowledgments
R.M. Pinto would like to acknowledge Fundação para a Ciência e
Tecnologia (FCT) for the Grant (SFRH/BD/40308/2007). This re-
search was supported in part by FCT Project POCTI/0303/2003
[21] E.A. Betterton, Crit. Rev. Environ. Sci. Technol. 33 (2003) 423–458.
[
[
22] S.G. Alvarez, M.T. Alvarez, Synthesis 1997 (1997) 413–414.
23] A. Morris, N. Jonathan, J.M. Dyke, P.D. Francis, N. Keddar, J.D. Mills, Rev. Sci.
Instrum. 55 (1984) 172–181.
(
Portugal).
[
[
24] K. Kimura, Handbook of HeI photoelectron spectra of fundamental organic
molecules: ionization energies, ab initio assignments, and valence electronic
structure for 200 molecules, Japan Scientific Societies Press, Halsted Press,
Tokyo, New York, 1981.
References
[
[
[
1] G. L’Abbé, Chem. Rev. 69 (1969) 345–363.
2] E.F.V. Scriven, K. Turnbull, Chem. Rev. 88 (1988) 297–368.
3] S.B. se, C. Gil, K. Knepper, V. Zimmermann, Angew. Chem., Int. Ed. 44 (2005)
25] M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R.
Cheeseman, J.A. Montgomery Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M.
Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G.
Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K.
Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao,
H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, V. Bakken, C.
Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R.
Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P.
Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C.
Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman,
J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu,
A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-
Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson,
W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople, Gaussian 03, Revision C.02,
Gaussian, Inc., Wallingford, CT, 2004.
5
188–5240.
4] P.L. Golas, N.V. Tsarevsky, K. Matyjaszewski, Macromol. Rapid Commun. 29
2008) 1167–1171.
[
(
[
[
5] G.O. Jones, K.N. Houk, J. Org. Chem. 73 (2008) 1333–1342.
6] D.P. Nguyen, H. Lusic, H. Neumann, P.B. Kapadnis, A. Deiters, J.W. Chin, J. Am.
Chem. Soc. 131 (2009) 8720–8721.
[
[
7] F. Amblard, J.H. Cho, R.F. Schinazi, Chem. Rev. 109 (2009) 4207–4220.
8] Y. Song, J.M. Chan, Z. Tovian, A. Secrest, E. Nagy, K. Krysiak, K. Bergan, M.A.
Parniak, E. Oldfield, Bioorg. Med. Chem. 16 (2008) 8959–8967.
9] J.A. Prescher, D.H. Dube, C.R. Bertozzi, Nature 430 (2004) 873–877.
[
[
10] A.B. Smith, I.G. Safonov, R.M. Corbett, J. Am. Chem. Soc. 124 (2002) 11102–
1113.
1
[
[
11] Q.S. Li, H.X. Duan, J. Phys. Chem. A 109 (2005) 9089–9094.
12] E.W. Meijer, S. Nijhuis, F.C.B.M.V. Vroonhoven, J. Am. Chem. Soc. 110 (1988)
[
[
[
[
[
26] R. Krishnan, J.S. Binkley, R. Seeger, J.A. Pople, J. Chem. Phys. 72 (1980) 650–654.
27] J.P. Santos, M.L. Costa, R.I. Olariu, F. Parente, Eur. Phys. J. D 39 (2006) 379–384.
28] T. Koopmans, Physica 1 (1934) 104–113.
29] C. Gonzalez, H.B. Schlegel, J. Phys. Chem. 94 (1990) 5523–5527.
30] A.P. Bruins, K.R. Jennings, S. Evans, Int. J. Mass Spectrom. Ion Process. 26 (1978)
7
209–7210.
[
[
13] H. Niino, T. Sato, A. Yabe, Appl. Phys. A: Mater. Sci. Process. 69 (1999) 145–148.
14] J.M. Dyke, A.P. Groves, A. Morris, J.S. Ogden, A.A. Dias, A.M.S. Oliveira, M.L.
Costa, M.T. Barros, M.H. Cabral, A.M.C. Moutinho, J. Am. Chem. Soc. 119 (1997)
395–404.
6
883–6887.
[
[
31] M. Karni, A. Mandelbaum, Org. Mass Spectrosc. 15 (1980) 53–64.
32] H. Schwarz, Organic Chemistry Topics in Current Chemistry, Springer, Berlin/
Heidelberg, 1978.
[
[
15] J.M. Dyke, A.P. Groves, A. Morris, J.S. Ogden, M.I. Catarino, A.A. Dias, A.M.S.
Oliveira, M.L. Costa, M.T. Barros, M.H. Cabral, A.M.C. Moutinho, J. Phys. Chem. A
1
03 (1999) 8239–8245.
[
[
33] D. Blachut, W. Danikiewicz, M. Olejnik, Z. Czarnocki, J. Mass Spectrom. 39
16] N. Hooper, L.J. Beeching, J.M. Dyke, A. Morris, J.S. Ogden, A.A. Dias, M.L. Costa,
M.T. Barros, M.H. Cabral, A.M.C. Moutinho, J. Phys. Chem. A 106 (2002) 9968–
(
2004) 966–972.
34] R.M. Pinto, A.A. Dias, M.L. Costa, J.P. Santos, J. Mol. Struct.: Theochem. 948
2010) 15–20.
9
975.
(
[
[
17] R.T.M. Fraser, N.C. Paul, M.J. Bagley, Org. Mass Spectrosc. 7 (1973) 83–88.
18] M.F. Duarte, F. Martins, M.T. Fernandez, G.J. Langley, P. Rodrigues, M.T. Barros,
M.L. Costa, Rapid Commun. Mass Spectrom. 17 (2003) 957–962.
[
[
35] V.G. Zakrzewski, J.V. Ortiz, J. Phys. Chem. 100 (1996) 13979–13984.
36] H. Bock, R. Dammel, J. Am. Chem. Soc. 110 (1988) 5261–5269.