Thermal behaviour of glycolic acid, sodium glycolate and its compounds with some

bivalent transition metal ions in the solid-state

A. L. C. S do Nascimento1, J. A. Teixeira1, W. D. G. Nunes1, D. J. C. Gomes2, O. Treu-

Filho1, C. Gaglieri, M. Pivatto4, F. J. Caires1,3, M. Ionashiro1

1Departamento de Química Analítica, Instituto de Química, Universidade Estadual Paulista (UNESP),

Araraquara, SP, Brazil.2Instituto Federal do Piauí, Campus Paulistana, Paulistana, PI, Brazil.3Departamento de Química, Faculdade de Ciências, Universidade Estadual Paulista (UNESP), Bauru, SP,

Brazil.4Instituto de Química, Universidade Federal de Uberlândia (UFU), Uberlândia, MG, Brazil

1Corresponding author. Tel. + 55 (14) 3103-6088E-mail address: caires.flavio@fc.unesp.br

203.9475

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Figure S1. HRESIMS spectrum of complex [Mn(gly)2]. The charged complex ion observed was [M – H]–.

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Figure S2. HRESIMS spectrum of complex [Co(gly)2]. The charged complex ion observed was [M – H]–.

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Figure S3. HRESIMS spectrum of complex [Ni(gly)2]. The charged complex ion observed was [M – H]–.

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Figure S4. HRESIMS spectrum of complex [Cu(gly)2]. The charged complex ion observed was [M]–.

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Figure S5. HRESIMS spectrum of complex [Zn(gly)2]. The charged complex ion observed was [M – H]–.

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Figure S6. X-ray powder diffraction patterns of the compounds.

Figure S7. Theoretical 3D structure of:the isomers: (a) coordinated by an oxygen of the

carboxylate group and the oxygen of the hydroxyl group and (b) coordinated by oxygen

of the carboxylate group.

Table S1. Theoretical geometry parameters of [MnL2].

[MnL2] Isomer A (trans) Isomer B (cis) Isomer CBond length (Å)Mn1-O2 1.88017

not optimized geometry

1.95978Mn1-O3 1.98052 2.02365Mn1-O4 1.88018 1.97103Mn1-O5 1.98060 2.04105Angles (°)O2-Mn1-O3 83.63 66.15O2-Mn1-O5 95.25 112.03O2-Mn1-O4 148.34 138.33O3-Mn1-O4 95.27 111.76O3-Mn1-O5 175.97 174.38O4-Mn1-O5 83.63 65.73

Figure S8. Theoretical 3D structure of the isomers: (a) and (b) coordinated by an

oxygen of the carboxylate group and the oxygen of the hydroxyl group in trans and cis

configuration, respectively and (c) coordinated by oxygen of the carboxylate group.

Table S2.Theoretical geometry parameters of [CoL2].

[CoL2] Isomer A (trans) Isomer B (cis) Isomer CBond length (Å)Co1-O2 1.85717 2.03370 1.93023Co1-O3 1.94276 1.89301 1.92781Co1-O4 1.85718 1.89297 1.93030Co1-O5 1.94275 2.03341 1.92776Angles (°)O2-Co1-O3 84.94 83.57 68.10O2-Co1-O5 95.35 92.64 111.89O2-Co1-O4 171.02 173.76 179.76O3-Co1-O4 95.37 100.65 111.91O3-Co1-O5 176.23 173.74 179.77O4-Co1-O5 84.93 83.55 68.10

Figura S9. Theoretical 3D structure of the isomers: (a) and (b) coordinated by an

oxygen of the carboxylate group and the oxygen of the hydroxyl group in trans and cis

configuration, respectively and (c) coordinated by oxygen of the carboxylate group.

Table S3. Theoretical geometry parameters of [NiL2].

[NiL2] Isomer A (trans) Isomer B (cis) Isomer CBond length (Å)Ni1-O2 1.84153 1.94123 1.91739Ni1-O3 1.88898 1.83097 1.91364Ni1-O4 1.84147 1.82939 1.91744Ni1-O5 1.88901 1.93571 1.91368Angles (°)O2-Ni1-O3 86.06 86.71 68.50O2-Ni1-O5 94.09 93.88 111.50O2-Ni1-O4 175.75 179.53 179.99O3-Ni1-O4 94.02 92.87 111.50O3-Ni1-O5 176.68 179.00 179.99O4-Ni1-O5 86.07 86.55 68.50

Figure S10. Theoretical 3D structure of the isomers: (a) and (b) coordinated by an

oxygen of the carboxylate group and the oxygen of the hydroxyl group in trans and cis

configuration, respectively and (c) coordinated by oxygen of the carboxylate group.

Table S4. Theoretical geometry parameters of [CuL2].

[CuL2] Isomer A (trans) Isomer B (cis) Isomer CBond length (Å)Cu1-O2 1.84538 2.03370 2.00964Cu1-O3 1.97927 1.89301 1.99930Cu1-O4 1.84455 1.89297 2.00956Cu1-O5 1.97845 2.03341 1.99925Angles (°)O2-Cu1-O3 85.68 83.57 65.76O2-Cu1-O5 92.27 92.64 114.23O2-Cu1-O4 130.39 173.76 179.80O3-Cu1-O4 93.30 100.65 114.25O3-Cu1-O5 176.53 173.74 179.64O4-Cu1-O5 85.88 83.55 65.76

Figure S11. Theoretical 3D structure of the isomers: (a) coordinated by an oxygen of

the carboxylate group and the oxygen of the hydroxyl group in trans configuration and

(b) coordinated by oxygen of the carboxylate group.

Table S5. Theoretical geometry parameters of [ZnL2].

[ZnL2] Isomer A (trans) Isomer B (cis) Isomer CBond length (Å)Zn1-O2 1.88860

not optimized geometry

2.03618Zn1-O3 2.11262 2.06929Zn1-O4 1.88858 2.06913Zn1-O5 2.11264 2.0368Angles (°)O2-Zn1-O3 82.23 64.62O2-Zn1-O5 110.93 138.13O2-Zn1-O4 153.94 135.60O3-Zn1-O4 110.93 132.82O3-Zn1-O5 121.05 135.63O4-Zn1-O5 82.23 64.62