A.W. Amick et al. / International Journal of Mass Spectrometry 316–318 (2012) 206–215
215
(11), 91 (61), 79 (10), 78 (12), 77 (16), 65 (9), 63 (4), 51 (11), and 39
(9).
Shawn C. Saylor, Melanie A. Vrabel, and Sarah B. Youngster. We
would also like to thank Washington College for generous monetary
support.
n-Propyl 3-phenylpropanoate (3). The general esterification
procedure was followed using dihydrocinnamic acid (502 mg,
3.34 mmol) and n-propanol (8.03 g, 134 mmol). IR (neat, cm−1):
1733 (C O). 1H (CDCl3, 400 MHz): ı 0.93 (t, 3H), 1.64 (sextet, 2H),
2.65 (t, 2H), 2.97 (t, 2H), 4.04 (t, 2H), 7.19–7.23 (m, 3H), 7.27–7.33
(m, 2H). MS (EI, 70 eV): m/z (%) 192 (31), 150 (12), 149 (4), 133 (24),
132 (2), 107 (43), 105 (50), 104 (100), 103 (11), 91 (85), 79 (14), 78
(14), 77 (19), 65 (9), 63 (4), 51 (11), 43 (16), 41 (11), and 39 (9).
Isopropyl 3-phenylpropanoate (4). The general esterification
procedure was followed using dihydrocinnamic acid (508 mg,
3.38 mmol) and isopropyl alcohol (7.86 g, 131 mmol). IR (neat,
cm−1): 1732 (C O). 1H (CDCl3, 400 MHz): ı 1.22 (d, 6H), 2.60 (t,
2H), 2.96 (t, 2H), 5.01 (septet, 1H), 7.18–7.23 (m, 3H), 7.26–7.32 (m,
2H). MS (EI, 70 eV): m/z (%) 192 (16), 150 (48), 149 (3), 133 (26),
132 (4), 107 (28), 105 (59), 104 (92), 103 (12), 91 (100), 79 (13), 78
(16), 77 (21), 65 (9), 63 (4), 51 (12), 43 (34), 41 (14), and 39 (12).
Ethyl 3-(3-thienyl)propanoate (5). The general esterification
procedure was followed using 3-(3-thienyl)propanoic acid (1.72 g,
11 mmol) and absolute ethanol (0.75 g, 16.5 mmol). IR (neat, cm−1):
1730 (C O). 1H (CDCl3, 400 MHz): ı 1.26 (t, 3H), 2.69 (t, 2H), 3.18
(t, 2H), 4.16 (q, 2H), 6.84 (d, 1H), 6.93 (t, 1H), 7.15 (d, 1H). MS (EI,
70 eV): m/z (%) 184 (32), 156 (3), 155 (11), 139 (9), 113 (35), 111
(32), 110 (67), 109 (5), 107 (3), 105 (3), 104 (6), 97 (100), 91 (6), 85
(5), 84 (5), 78 (4), 77 (8), 71 (3), 69 (4), 67 (5), 66 (3), 65 (5), 63 (2),
58 (4), 57 (2), 53 (7), 51 (5), 50 (2), 45 (16), 43 (2), 42 (2), 41 (3), and
39 (12).
Ethyl 4-phenylbutanoate (6). The general esterification pro-
cedure was followed using 4-phenylbutanoic acid (495 mg,
3.01 mmol) and absolute ethanol (7.89 g, 171 mmol). IR (neat,
cm−1): 1732 (C O). 1H (CDCl3, 400 MHz): ı 1.27 (t, 3H), 1.97 (quin-
tet, 2H), 2.33 (t, 2H), 2.67 (t, 2H), 4.13 (q, 2H), 7.17–7.23 (m, 3H),
7.26–7.33 (m, 2H). MS (EI, 70 eV): m/z (%) 192 (22), 147 (49), 146
(33), 118 (4), 117 (18), 116 (2), 115 (7), 105 (29), 104 (79), 103 (7),
92 (9), 91 (100), 90 (3), 89 (7), 88 (55), 79 (4), 78 (8), 77 (10), 74 (9),
70 (15), 65 (25), 63 (7), 61 (24), 59 (38), 51 (10), 50 (3), 45 (7), 43
(8), 42 (4), 41 (10), and 39 (14).
Ethyl phenylacetate (7). The general esterification procedure
was followed using phenylacetic acid (509 mg, 3.74 mmol) and
absolute ethanol (7.89 g, 171 mmol). IR (neat, cm−1): 1732 (C O).
1H (CDCl3, 400 MHz): ı 1.25 (t, 3H), 3.63 (s, 2H), 4.16 (q, 2H),
7.25–7.37 (m, 5H). MS (EI, 70 eV): m/z (%) 164 (16), 119 (2), 105
(2), 92 (12), 91 (100), 90 (3), 89 (4), 65 (13), 63 (4), 51 (3), 43 (4),
41 (2), and 39 (6).
Appendix A. Supplementary data
Supplementary data associated with this article can be found, in
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(ref.
26),
IE(H•) = 13.60 eV,
PA[C3H7C(O)OCH3] = 836 kJ
mol−1
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2048–2054.
This collaboration originates from an intense discussion on how
to present mass spectrometry and gas-phase ion chemistry in a
textbook for beginners (see Ref. 9a). As one of the results, we have
learnt that the title compound represents a non-trivial example.
All the more, we would like to thank the following investigators for
their assistance in the early stages of this project: Jason F. Boyer,