Synthesis and Chemistry of 1,3-Dihydrotelluroloquinoxaline and Derivatives: Crystal and Molecular Structure of 1,3-Dihydro-2,2-diiodo-2λ4-telluroloquinoxaline-2,3-Bis(iodomethyl)quinoxaline (1:1)

DOI: 10.1039/DT9840000023

Source and publish data:

Journal of the Chemical Society, Dalton Transactions p. 23 - 28 (1984)

Update date:2022-08-30

Topics:

Authors:

Singh, Harkesh B.

McWhinnie, William R.

Hamor, Thomas A.

Jones, Richard H.

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Article abstract of DOI:10.1039/DT9840000023

The reaction of 2,3-bis(bromomethyl)quinoxaline with tellurium and sodium iodide (2 h) gave the violet compound 1,3-dihydro-2,2-di-iodo-2λ⁴-tellurolo<3,4-b>quinoxaline (m.p. 158-160 deg C).The latter compound readily forms a black 1:1 complex with 7,7,8,8-tetracyanoquinodimethane.The u.v., n.m.r., i.r., and mass spectra of the new organotellurium heterocycles are presented and discussed. 2,3-Bis(bromomethyl)quinoxaline also reacts with tellurium and potassium iodide (1 h) to give a yellow material for which elemental analysis, n.m.r., and mass spectroscopy suggest a 1:1 adduct of the above di-iodo-complex and 2,3-bis(iodomethyl)quinoxaline.Sodium hydrogentelluride reduces 2,3-bis(bromomethyl)quinoxaline to 2,3-dimethylquinoxaline.The crystal and molecular structure of the 1:1 adduct of 1,3-dihydrotelluro<3,4-b>quinoxaline, C10H8I2N2Te, with 2,3-bis(iodomethyl)quinoxaline, C10H8I2N2, has been determined.Crystals of the compound are triclinic, space group P<*>, with a = 7.667(2), b = 11.826(4), c = 13.739(4) Angstroem, α = 93.26(3), β = 98.37(2), γ = 83.29(2) deg, and Z = 2.Final R = 0.059 for 2998 observed reflexions.The structure consists of discrete molecules of C10H8I2N2Te and C10H8I2N2, a pair of each being linked into centrosymmetric dimers by weak T<*>I linkages.The co-ordination about tellurium is a distorted octahedron with two Te-C bonds <2.14(1) Angstroem>, two axial Te-I bonds <2.886(2), 2.911(2) Angstroem> and two longer equatorial Te-I bonds trans to Te-C <3.761(2), 3.788(2) Angstroem>, the longer contact being to an iodine of the organic di-iodide.Large deviations of bond angle from the ideal octahedral angles occur.A further very weak interaction links the dimers into chains along x.No abnormal features are observed in the organic moieties.