Supplementary Material for
Infrared spectroscopy of copper-resveratrol complexes: a joint experimental and
theoretical study
B. Chiavarino1 M. E. Crestoni1 S. Fornarini1 S. Taioli 2,3,4,5 I. Mancini3 P. Tosi3
2
1
Faculty of Pharmacy and Medicine, Sapienza - Università di Roma, Piazzale A. Moro 5, 00185 Rome, Italy
Interdisciplinary Laboratory for Computational Science, FBK-CMM and University of Trento, via Sommarive 18, 38123
Trento, Italy
3
Department of Physics, University of Trento, Via Sommarive 14, 38123 Trento, Italy
4
Istituto Nazionale di Fisica Nucleare, Sezione di Perugia, Italy
5
Department of Chemistry, University of Bologna, Via F. Selmi 2, I-40126 Bologna, Italy
Contents
Fig. 1S: ESI(+)-MS spectrum obtained from a 1:1 resveratrol/CuSO4 solution 10-4 M in methanol/water (1:1). The
ion at m/z 228 is Resv+●. The second major ion at m/z 519 is [Cu(Resv)2]+. The ion at m/z 455 corresponds to a
dehydrodimer of resveratrol.
Fig. 2S: IR spectrum (blue line) calculated for Resv+● at B3LYP/6-311+G** level of theory, in the 1100-1800 cm-1
range. IR frequencies are scaled by 0.972. The experimental IRMPD spectrum is reported in the red profile.
Fig. 3S: IR spectrum (blue line) calculated for Resv+● at B3LYP/6-311+G** level of theory, in the 3500-3700 cm-1
range. IR frequencies are scaled by 0.955. The experimental IRMPD spectrum is reported in the red profile.
Fig. 4S: IR spectrum (blue line) calculated for the [Cu(Resv)2]+ complex at B3LYP/6-31G* level of theory, in the
1100-1800 cm-1 range. IR frequencies are scaled by 0.955. The experimental IRMPD spectrum is reported in the
red profile.
Fig. 5S: IR spectrum (blue line) calculated for the [Cu(Resv)2]+ complex at B3LYP/6-31G* level of theory, in the
3500-3700 cm-1 range. IR frequencies are scaled by 0.972. The experimental IRMPD spectrum is reported in the
red profile.
Fig. 6S: IR spectrum (blue line) calculated for the [Cu(Resv)]+ complex at B3LYP/6-31G* level of theory, in the
1100-1700 cm-1 range. IR frequencies are scaled by 0.955. The green line is the IR spectrum calculated in the
DFPT framework as described in the text. The experimental IRMPD spectrum is reported in the red profile.
Fig. 7S: IR spectrum (blue line) calculated for the [Cu(Resv)]+ complex at B3LYP/6-31G* level of theory, in the
3500-3700 cm-1 range. IR frequencies are scaled by 0.972. The green line is the IR spectrum calculated in the
DFPT framework as described in the text. The experimental IRMPD spectrum is reported in the red profile.
Please note: in Figures 2S-7S scaling factors for the calculated IR frequencies are adopted on the basis of the
good agreement with the experimental frequencies (J. Steill, J. Zhao, C.-K. Siu, Y. Ke, U. H. Verkerk, J.
Oomens, R. C. Dunbar, A. C. Hopkinson, and K. W. M. Siu, Angew. Chem., Int. Ed. 47, 9666(2008)).
Intens.
× 105
228.2
6
519.2
4
2
455.3
309.2
100
200
300
400
500
m/z
600
Fig. 1S: ESI(+)-MS spectrum obtained from a 1:1 resveratrol/CuSO4 solution 10-4 M in methanol/water (1:1). The
ion at m/z 228 is Resv+●. The second major ion at m/z 519 is [Cu(Resv)2]+. The ion at m/z 455 corresponds to a
dehydrodimer of resveratrol.
1100
1200
1300
1400
1500
1600
1700
1800
Wavenumber (cm-1)
Fig. 2S: IR spectrum (blue line) calculated for Resv+● at B3LYP/6-311+G** level of theory, in the 1100-1800 cm-1
range. IR frequencies are scaled by 0.972. The experimental IRMPD spectrum is reported in the red profile.
3500
3550
3600
3650
3700
Wavenumber (cm-1)
Fig. 3S: IR spectrum (blue line) calculated for Resv+● at B3LYP/6-311+G** level of theory, in the 3500-3700 cm-1
range. IR frequencies are scaled by 0.955. The experimental IRMPD spectrum is reported in the red profile.
1100
1200
1300
1400
1500
1600
1700
1800
Wavenumber (cm-1)
Fig. 4S: IR spectrum (blue line) calculated for the [Cu(Resv)2]+ complex at B3LYP/6-31G* level of theory, in the
1100-1800 cm-1 range. IR frequencies are scaled by 0.955. The experimental IRMPD spectrum is reported in the
red profile.
3500
3550
3600
3650
3700
Wavenumber (cm-1)
Fig. 5S: IR spectrum (blue line) calculated for the [Cu(Resv)2]+ complex at B3LYP/6-31G* level of theory, in the
3500-3700 cm-1 range. IR frequencies are scaled by 0.972. The experimental IRMPD spectrum is reported in the
red profile.
1100
1200
1300
1400
1500
1600
1700
Wavenumber (cm-1)
Fig. 6S: IR spectrum (blue line) calculated for the [Cu(Resv)]+ complex at B3LYP/6-31G* level of theory, in the
1100-1700 cm-1 range. IR frequencies are scaled by 0.955. The green line is the IR spectrum calculated in the
DFPT framework as described in the text. The experimental IRMPD spectrum is reported in the red profile. It is
to be noted that the experimental spectrum is only partial, covering the frequency ranges of the expected most
pronounced activity. In fact this complex is hardly active in IRMPD and required relatively long acquisition times
(2s).
3500
3550
3600
3650
3700
Wavenumber (cm-1)
Fig. 7S: IR spectrum (blue line) calculated for the [Cu(Resv)]+ complex at B3LYP/6-31G* level of theory, in the
3500-3700 cm-1 range. IR frequencies are scaled by 0.972. The green line is the IR spectrum calculated in the
DFPT framework as described in the text. The experimental IRMPD spectrum is reported in the red profile.