Wikipedia

2,3-Butanediamine

2,3-Butanediamine are organic compounds with the formula CH3CH(NH2)CH(NH2)CH3. Three stereoisomers exist, meso and a pair of enantiomers. These diamines form complexes with transition metals.[3]

2,3-Butanediamine
Names
Other names
1,2-Dimethylethylenediamine
2,3-Diaminobutane
Butane-2,3-diamine
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C4H12N2/c1-3(5)4(2)6/h3-4H,5-6H2,1-2H3
    Key: GHWVXCQZPNWFRO-UHFFFAOYSA-N
  • (S,S): InChI=1S/C4H12N2/c1-3(5)4(2)6/h3-4H,5-6H2,1-2H3/t3-,4-/m0/s1
    Key: GHWVXCQZPNWFRO-IMJSIDKUSA-N
  • rel-(R,S): InChI=1S/C4H12N2/c1-3(5)4(2)6/h3-4H,5-6H2,1-2H3/t3-,4+
    Key: GHWVXCQZPNWFRO-ZXZARUISSA-N
  • NC(C)C(N)C
  • (S,S): C[C@@H]([C@H](C)N)N
  • rel-(R,S): C[C@H]([C@H](C)N)N
Properties
C4H12N2
Molar mass 88.154 g·mol−1
Appearance colorless oil
Boiling point 44-45 °C (25 mmHg, rac)
46-48 °C (25 mmHg, meso)[1]
55.3-59.3 °C (60 mmHg, DL-threo)
56.1-60.5 °C (60 mmHg, meso)[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Synthesis

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2,3-Butanediamines can be prepared by hydrolyzing 2-ethoxy-4,5-dihydro-4,5-dimethylimidazole with barium hydroxide.[4] Alternative, it is produced by reduction of dimethylglyoxime with lithium aluminium hydride.[5] The meso and the d,l diastereomers can be separated by fractional crystallization of the hydrochlorides. The enantiomers have been resolved using tartrate salts.[6]

Reactions

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Structure of the cation [Co(meso-bn)2CO3]+ as determined by X-ray crystallography. Color code: red = N, blue = N.

In coordination chemistry, 2,3-butanediamine (abbreviated bn) has illuminates aspects of the stereochemistry. The structure of [Co(meso-2,3-butanediamine)2CO3]+ confirms the presence of the rarely observed axial methyl groups on each of the diamine-cobalt rings.[7]

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References

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  1. ^ Fred Basolo, R. Kent Murmann, and Yun Ti Chen. Dissociation Constants of Substituted Ethylenediamines. J. Am. Chem. Soc. 1953, 75, 6, 1478–1480. doi:10.1021/ja01102a507.
  2. ^ Robert Ghirardelli and Howard J. Lucas. Stereochemistry of the Opening of the Imine Ring with Ethylamine. J. Am. Chem. Soc. 1957, 79, 3, 734–741. doi:10.1021/ja01560a064.
  3. ^ Tsuchiya, Ryokichi; Uehara, Akira; Yoshikuni, Tadatsugu (1982). "Solid-phase thermal cis-trans isomerization of bis(diamine)chromium(III) complexes containing d,l-2,3-butanediamine, d,l-1,2-cyclohexanediamine, or d,l-2,4-pentanediamine". Inorganic Chemistry. 21 (2): 590–594. doi:10.1021/ic00132a025.
  4. ^ Harold Kohn and Sang Hun Jung. New stereoselective method for the preparation of vicinal diamines from olefins and cyanamide. Journal of the American Chemical Society 1983 105 (12), 4106-4108. doi:10.1021/ja00350a068.
  5. ^ Hilleary, Christopher J.; Them, Theodore F.; Tapscott, Robert E. (1980). "Stereochemical studies on diastereomers of tris(2,3-butanediamine)cobalt(III)". Inorganic Chemistry. 19: 102–107. doi:10.1021/ic50203a022.
  6. ^ Dickey, F. H.; Fickett, Wildon; Lucas, H. J. (1952). "Stereoisomeric 2,3-Butanediamines, 3-Amino-2-butanols and 2,3-Dimethylethyleneimines; Stereochemistry of the Opening and Closing of the Imine Ring1". Journal of the American Chemical Society. 74 (4): 944–951. doi:10.1021/ja01124a023.
  7. ^ Duesler, E. N.; Fe Gargallo, M.; Tapscott, R. E. (1982). "Structure of lel lel lel tris[(±)-2,3-butanediamine]-cobalt(III) chloride". Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry. 38 (4): 1300–1303. Bibcode:1982AcCrB..38.1300D. doi:10.1107/S0567740882005585.
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