関: hydrogensulfite、hydrosulfite

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/09/12 04:11:18」(JST)

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A ball-and-stick model of the most commonly stated structure (the one having C_3v symmetry) for the bisulfite ion in solution and in the solid state. Note that the hydrogen is bonded to the sulfur atom.

Bisulfite ion (IUPAC-recommended nomenclature: hydrogen sulfite) is the ion HSO₃⁻. Salts containing the HSO₃⁻ ion are termed bisulfites also known as sulfite lyes. For example, sodium bisulfite is NaHSO₃.

Structure

Bisulfite tautomers in equilibrium

Ball-and-stick models of the proposed bisulfite equilibrium. The tautomer on the right has C_3v symmetry.

Some evidence may suggest that the proton in bisulfite ion is located on sulfur, giving rise to C_3v symmetry. There is, however, some evidence from ¹⁷O NMR spectroscopy to suggest that two tautomeric forms of HSO₃⁻ exist in dynamic equilibrium, one which has the proton attached to sulfur (HSO₃⁻) and one which is protonated at oxygen (HOSO₂⁻).^[1] The C_3v structure is supported by X-ray crystallography and, in aqueous solution, by Raman spectroscopy (ν(S–H) = 2500 cm⁻¹).

Reactions

Bisulfite salts are typically prepared by treatment of alkaline solutions with excess sulfur dioxide:

SO₂ + NaOH → NaHSO₃

HSO₃⁻ is the conjugate base of sulfurous acid, H₂SO₃:

H₂SO₃ ⇌ HSO₃⁻ + H⁺

Sulfurous acid is not an isolable compound and does not appear to exist in solution either. An equilibrium that is much more consistent with spectroscopic evidence is given :

SO₂ + H₂O ⇌ HSO₃⁻ + H⁺

HSO₃⁻ is a weak acidic species with a pK_a of 6.97. Its conjugate base is the sulfite ion, SO₃²⁻:

HSO₃⁻ ⇌ SO₃²⁻ + H⁺

Bisulfites are reducing agents, as are all sulfites and sulfur dioxide, which contains sulfur in the same oxidation state (+4).

Medicine

Bisulfite salts are common additives to the drug epinephrine in order to prevent its oxidation to adrenochrome and resulting inactivation. Bisulfites can sometimes cause an allergic reaction. This is different from the common sulfa drugs allergy. The quantity of bisulfite in medical pain blockers that initiates Type 1 hypersensitivity has been determined by Fraser and Huang.^[2]

References

^ D. A. Horner, R. E. Connick, Inorg. Chem. 25, 2414-7 (1986).
^ Fraser, WA, and Huang, AS: Are sulfites really safe? NEJM, 311:542, Aug. 23, 1984

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English Journal

The challenging SO2-mediated chemical build-up of protein aggregates in wines.

Chagas R1, Ferreira LM2, Laia CA2, Monteiro S3, Ferreira RB4.
Food chemistry.Food Chem.2016 Feb 1;192:460-9. doi: 10.1016/j.foodchem.2015.07.052. Epub 2015 Jul 11.
Despite the extensive research performed during the last decades, the multifactorial mechanism responsible for white wine protein haze formation is not fully characterized. A model is proposed, which is essentially based on two postulates: the experimental identification of sulfur dioxide as the non
PMID 26304373

Alterations in DNA-methylation of the dopamine-receptor 2 gene are associated with abstinence and health care utilization in individuals with a lifetime history of pathologic gambling.

Hillemacher T1, Frieling H2, Buchholz V2, Hussein R2, Bleich S3, Meyer C4, John U4, Bischof A5, Rumpf HJ5.
Progress in neuro-psychopharmacology & biological psychiatry.Prog Neuropsychopharmacol Biol Psychiatry.2015 Dec 3;63:30-4. doi: 10.1016/j.pnpbp.2015.05.013. Epub 2015 May 28.
BACKGROUND: Several studies point towards a role for dopaminergic circuits in the pathophysiology of problematic gambling behavior. The aim of the present study was to investigate alterations of DNA methylation in the dopamine D2 receptor (DRD2)-gene in participants with pathologic gambling behavior
PMID 26028496

A novel flavone-based fluorescent probe for relay recognition of HSO3(-) and Al(3.).

Xu S1, Tang R2, Wang Z1, Zhou Y1, Yan R1.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.Spectrochim Acta A Mol Biomol Spectrosc.2015 Oct 5;149:208-15. doi: 10.1016/j.saa.2015.04.072. Epub 2015 Apr 29.
In this work, a new flavone-based fluorescent probe 3-hydroxy-3'-formylflavone (3HFF) was designed to achieve highly selective relay recognition of HSO3(-) and Al(3+) in DMSO-H2O (2:8, v/v) solution. 3HFF displayed a highly selective response to HSO3(-) with a green fluorescence appearing at 524nm.
PMID 25965168

Japanese Journal

Prediction of the Stability of Meropenem in Intravenous Mixtures

Takasu Yuko,Yoshida Miyako,Tange Mio [他]
Chemical and pharmaceutical bulletin 63(4), 248-254, 2015-04
NAID 40020412091

逆浸透膜を用いた低環境負荷海水淡水化プロセス

膜 40(2), 86-90, 2015
… The influence of addition of sodium hypochlorite and sodium bisulfite to reverse osmosis (RO)process was exam-ined quantitatively by parallel tests of several pilot-scale UF+RO units. …
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Prediction of the Stability of Meropenem in Intravenous Mixtures

, , , ,
Chemical and Pharmaceutical Bulletin 63(4), 248-254, 2015
… The hydrolysis of meropenem in aqueous solution was found to be accelerated by pH, and by increasing concentrations of sodium bisulfite (SBS) and L-cysteine. …
NAID 130005061426