Supplementary Material Manuscript VLPecoraro3,5-Di-iso-propylpyrazole1 (4.05 g, 26 mmol) was heated...
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Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2008 1 Supplementary Material for the Manuscript Corroborative Cobalt and Zinc model compounds of α-amino-β-carboxymuconic-ε- semialdehyde decarboxylase (ACMSD) Jessica Gätjens, a,‡ Christopher S. Mullins, a Jeff W. Kampf, a Pierre Thuéry, b and Vincent L. Pecoraro a∗ a University of Michigan, Department of Chemistry, Willard H. Dow Laboratories, 930 North University, Ann Arbor, MI 48109, USA b CEA-Saclay, IRAMIS, SCM, LCCEf, F-91191 Gif-sur-Yvette, France. ∗ Corresponding author: [email protected] , phone: +1-734-7611519; fax: +1-734-6474865. ‡ present address: Universität Wien, Institut für Anorganische Chemie, Währinger Straße 42, A-1090 Wien, Austria
Transcript of Supplementary Material Manuscript VLPecoraro3,5-Di-iso-propylpyrazole1 (4.05 g, 26 mmol) was heated...
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Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2008
1
Supplementary Material for the Manuscript
Corroborative Cobalt and Zinc model
compounds of α-amino-β-carboxymuconic-ε-
semialdehyde decarboxylase (ACMSD)
Jessica Gätjens,a,‡ Christopher S. Mullins,a Jeff W. Kampf,a Pierre Thuéry,b and
Vincent L. Pecoraroa∗
a University of Michigan, Department of Chemistry, Willard H. Dow Laboratories, 930
North University, Ann Arbor, MI 48109, USA
b CEA-Saclay, IRAMIS, SCM, LCCEf, F-91191 Gif-sur-Yvette, France.
∗ Corresponding author: [email protected], phone: +1-734-7611519; fax: +1-734-6474865. ‡ present address: Universität Wien, Institut für Anorganische Chemie, Währinger Straße 42, A-1090 Wien, Austria
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Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2008
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1. Synthesis of ligand precursor 3,5-di-iso-propylpyrazole-1-methanol.
3,5-Di-iso-propylpyrazole1 (4.05 g, 26 mmol) was heated to 50-60 °C with 95 mL of
water. Then heating was stopped and 37% aq. formaldehyde solution (37 mL) was
added. The solution was heated to 80-90 °C for 6 h and stirred at room temperature
overnight. The aqueous solution was extracted with dichloromethane, the organic
phase was dried with MgSO4 and the solvent was evaporated to yield a white solid.
Yield 4.7 g (98%).
1H NMR (300 MHz, CDCl3): δ [ppm] 6.32 (OH), 5.87 (pz H4), 5.48, 5.46 (s, CH2), 3.12
– 2.85 (m, iPr-CH), 1.30, 1.28, 1.21, 1.18 (s, CH3).
2. UV-vis spectra for 3
Fig. S1. UV-vis spectra of 3 in acetonitrile/toluene (1:1), left, and in methanol, right; c
= 1 x 10-3 M.
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Supp
lem
enta
ry M
ater
ial (
ESI)
for D
alto
n Tr
ansa
ctio
ns
This
jour
nal i
s © T
he R
oyal
Soc
iety
of C
hem
istry
200
8
3
Tabl
e S1
. Mai
n bo
nd le
ngth
s (Å
) and
ang
les
(°) f
or c
ompl
exes
1 –
3, 5
, 6, 7
.
1 2
3a)
5a)
6 7
Co(
1)-C
l(1)
Co(
1)-O
(1)
Co(
1)-N
(1)
Co(
1)-N
(3)
Co(
1)-N
(5)
O(1
)-Co(
1)-N
(1)
O(1
)-Co(
1)-N
(3)
O(1
)-Co(
1)-N
(5)
N(1
)-C
o(1)
-N(3
) N
(1)-
Co(
1)-N
(5)
N(3
)-C
o(1)
-N(5
) C
l(1)-
Co(
1)-O
(1)
Cl(1
)-C
o(1)
-N(1
) C
l(1)-
Co(
1)-N
(3)
Cl(1
)-C
o(1)
-N(5
)
2.28
81(8
) 1.
9826
(18)
2.
302(
2)
2.05
6(2)
2.
061(
2)
77.0
0(7)
11
9.50
(8)
117.
22(8
) 76
.83(
8)
77.4
7(8)
10
8.67
(9)
94.7
0(5)
17
1.50
(6)
106.
23(7
) 10
8.46
(6)
Co(
1)-C
l(1)
Co(
1)-O
(1)
Co(
1)-N
(1)
Co(
1)-N
(3)
Co(
1)-N
(5)
O(1
)-Co(
1)-N
(1)
O(1
)-Co(
1)-N
(3)
O(1
)-Co(
1)-N
(5)
N(1
)-C
o(1)
-N(3
) N
(1)-
Co(
1)-N
(5)
N(3
)-C
o(1)
-N(5
) C
l(1)-
Co(
1)-O
(1)
Cl(1
)-C
o(1)
-N(1
) C
l(1)-
Co(
1)-N
(3)
Cl(1
)-C
o(1)
-N(5
)
2.30
09(1
0)
1.99
8(2)
2.
263(
3)
2.06
3(3)
2.
057(
3)
77.1
5(10
) 11
3.96
(11)
11
7.38
(11)
76
.02(
10)
77.0
8(11
) 11
3.39
(11)
98
.11(
8)
174.
70(8
) 10
8.35
(8)
103.
39(8
)
Co(
1)-O
(1)
Co(
1)-O
(3)
Co(
1)-N
(1)
Co(
1)-N
(3)
Co(
1)-N
(5)
Co(
1)-O
(2)#
1 O
(1)-C
o(1)
-N(1
) O
(1)-C
o(1)
-N(3
) O
(1)-C
o(1)
-N(5
) O
(1)-C
o(1)
-O(3
) O
(1)-C
o(1)
-O(2
)#1
N(1
)-C
o(1)
-N(3
) N
(1)-
Co(
1)-N
(5)
N(1
)-C
o(1)
-O(3
) N
(1)-
Co(
1)-O
(2)#
1 N
(3)-
Co(
1)-N
(5)
N(3
)-C
o(1)
-O(3
) N
(3)-
Co(
1)-O
(2)#
1 N
(5)-
Co(
1)-O
(3)
N(5
)-C
o(1)
-O(2
)#1
O(3
)-Co(
1)-O
(2)#
1
2.06
8(4)
2.
093(
4)
2.22
9(4)
2.
127(
4)
2.13
9(4)
2.
051(
4)
79.6
1(15
) 87
.96(
15)
92.3
6(15
) 17
7.17
(16)
86
.53(
14)
78.1
0(16
) 79
.27(
16)
101.
36(1
5)
166.
10(1
4)
156.
92(1
8)
89.6
4(17
) 10
2.66
(16)
90
.43(
17)
100.
39(1
6)
92.5
3(15
)
Zn(1
)-O
(1)
Zn(1
)-O
(3)
Zn(1
)-N(1
) Zn
(1)-N
(3)
Zn(1
)-N(5
) Zn
(1)-
O(4
) O
(1)-Z
n(1)
-N(1
) O
(1)-Z
n(1)
-N(3
) O
(1)-Z
n(1)
-N(5
) O
(1)-Z
n(1)
-O(3
) O
(1)-Z
n(1)
-O(4
) N
(1)-
Zn(1
)-N
(3)
N(1
)-Zn
(1)-
N(5
) N
(1)-
Zn(1
)-O
(3)
N(1
)-Zn
(1)-
O(4
) N
(3)-
Zn(1
)-N
(5)
N(3
)-Zn
(1)-
O(3
) N
(3)-
Zn(1
)-O
(4)
N(5
)-Zn
(1)-
O(3
) N
(5)-
Zn(1
)-O
(4)
O(3
)-Zn(
1)-O
(4)
2.12
4(4)
2.
115(
4)
2.13
8(5)
2.
343(
4)
2.10
7(5)
2.
016(
4)
86.6
4(16
) 76
.11(
14)
92.1
0(16
) 17
7.61
(15)
83
.69(
14)
76.2
6(15
) 15
1.42
(16)
92
.42(
16)
102.
42(1
5)
75.7
2(16
) 10
5.81
(14)
15
9.80
(14)
89
.78(
16)
105.
82(1
6)
94.3
7(15
)
Co(
1)-N
(1)
Co(
1)-N
(3)
Co(
1)-N
(4)
Co(
1)-N
(6)
Co(
1)-O
(1)
N(1
)-C
o(1)
-N(3
) N
(1)-
Co(
1)-N
(4)
N(1
)-C
o(1)
-N(6
) N
(1)-
Co(
1)-O
(1)
N(3
)-C
o(1)
-N(4
) N
(3)-
Co(
1)-N
(6)
N(3
)-C
o(1)
-O(1
) N
(4)-
Co(
1)-N
(6)
N(4
)-C
o(1)
-O(1
) N
(6)-
Co(
1)-O
(1)
2.02
2(2)
2.
343(
2)
2.06
4(2)
2.
088(
2)
2.05
10(1
8)
77.1
0(7)
11
1.52
(8)
101.
70(8
) 13
8.76
(8)
76.3
5(8)
17
4.80
(9)
87.7
6(7)
99
.60(
9)
101.
46(7
) 96
.31(
8)
Co(
1)-N
(1)
Co(
1)-N
(3)
Co(
1)-N
(4)
Co(
1)-O
(1)
Co(
1)-O
(3)
N(1
)-C
o(1)
-N(3
)N
(1)-
Co(
1)-N
(4)
N(1
)-C
o(1)
-O(1
)N
(1)-
Co(
1)-O
(3)
N(3
)-C
o(1)
-N(4
)N
(3)-
Co(
1)-O
(1)
N(3
)-C
o(1)
-O(3
)N
(4)-
Co(
1)-O
(1)
N(4
)-C
o(1)
-O(3
)O
(1)-C
o(1)
-O(3
)
2.03
2(4)
2.
288(
4)
2.01
4(4)
2.
026(
3)
1.98
9(3)
78
.72(
14)
112.
11(1
5)
104.
40(1
5)
110.
18(1
4)
78.7
8(14
) 17
6.87
(14)
86
.69(
14)
100.
07(1
4)
131.
17(1
5)
91.9
5(12
)
a) o
nly
one
subu
nit i
s pr
esen
ted
-
Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2008
4
Table S2: Hydrogen bonds for complexes 2, 3, 5-7 [Å and deg].
D-H...A d(D-H) d(H...A) d(D...A)
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Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2008
5
References
1) N. Kitajima, K. Fujisawa, C. Fujimoto, Y. Maro-oka, S. Hashimoto, T.
Kitagawa, K. Toriumi, K. Tatsumi and A. Nakamura, J. Am. Chem. Soc., 1992, 114,
1277-1291.
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