Aromatic Versus Heteroradialene Character in Extended Thiophloroglucinol Ligands and their Trinuclear Nickel(II) Complexes

Feldscher B, Stammler A, Bögge H, Glaser T (2014)
Chemistry - An Asian Journal 9(8): 2205-2218.

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Abstract
Extended phloroglucinol ligands and complexes are best described as nonaromatic heteroradialenes. Herein, the electronic structures of extended thiophloroglucinol ligands and their Ni-3(II) complexes are evaluated by comparison to their phloroglucinol analogs by means of NMR, FTIR, UV/Vis, and structural parameters. To provide a full set of compounds for this comparison of S versus O substitution, a new triplesalen ligand, its Ni-3(II) complex, and a new thiophloroglucinol were synthesized. H-1 and N-15 NMR chemical shifts and coupling constants prove that the thiophloroglucinol ligands exist as the N-protonated and not the O-protonated tautomer. C-13 and N-15 NMR chemical shifts and structural parameters further demonstrated that the extended thiophloroglucinol ligands must be described with a predominant thione-enamine (heteroradialene) character despite the participation of a C=S double bond. In the Ni-3(II) complexes, this heteroradialene character is reduced but still predominant.
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Feldscher B, Stammler A, Bögge H, Glaser T. Aromatic Versus Heteroradialene Character in Extended Thiophloroglucinol Ligands and their Trinuclear Nickel(II) Complexes. Chemistry - An Asian Journal. 2014;9(8):2205-2218.
Feldscher, B., Stammler, A., Bögge, H., & Glaser, T. (2014). Aromatic Versus Heteroradialene Character in Extended Thiophloroglucinol Ligands and their Trinuclear Nickel(II) Complexes. Chemistry - An Asian Journal, 9(8), 2205-2218.
Feldscher, B., Stammler, A., Bögge, H., and Glaser, T. (2014). Aromatic Versus Heteroradialene Character in Extended Thiophloroglucinol Ligands and their Trinuclear Nickel(II) Complexes. Chemistry - An Asian Journal 9, 2205-2218.
Feldscher, B., et al., 2014. Aromatic Versus Heteroradialene Character in Extended Thiophloroglucinol Ligands and their Trinuclear Nickel(II) Complexes. Chemistry - An Asian Journal, 9(8), p 2205-2218.
B. Feldscher, et al., “Aromatic Versus Heteroradialene Character in Extended Thiophloroglucinol Ligands and their Trinuclear Nickel(II) Complexes”, Chemistry - An Asian Journal, vol. 9, 2014, pp. 2205-2218.
Feldscher, B., Stammler, A., Bögge, H., Glaser, T.: Aromatic Versus Heteroradialene Character in Extended Thiophloroglucinol Ligands and their Trinuclear Nickel(II) Complexes. Chemistry - An Asian Journal. 9, 2205-2218 (2014).
Feldscher, Bastian, Stammler, Anja, Bögge, Hartmut, and Glaser, Thorsten. “Aromatic Versus Heteroradialene Character in Extended Thiophloroglucinol Ligands and their Trinuclear Nickel(II) Complexes”. Chemistry - An Asian Journal 9.8 (2014): 2205-2218.
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