Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Thiocyanic acid is a chemical compound with the formula HSCN which exists as a tautomer with isothiocyanic acid (HNCS). The iso- form tends to dominate with the material being about 95% isothiocyanic acid in the vapor phase.
Tautomerism between thiocyanic acid (left) and isothiocyanic acid (right)
It is a moderately strong acid, with a pKa of 1.1 at 20 °C and extrapolated to zero ionic strength.
HSCN is predicted to have a triple bond between carbon and nitrogen. It has been observed spectroscopically but has not been isolated as a pure substance.
The salts and esters of thiocyanic acid are known as thiocyanates. The salts are composed of the thiocyanate ion (−SCN) and a suitable metal cation (e.g., potassium thiocyanate, KSCN). The esters of thiocyanic acid have the general structure R–SCN.
Isothiocyanic acid, HNCS, is a Lewis acid whose free energy, enthalpy and entropy changes for its 1:1 association with a variety of Lewis bases in carbon tetrachloride solution at 25°C have been reported. HNCS acceptor properties are discussed in the ECW model.
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^Richter, Victor von; Spielmann, Percy E., trans. (1922). Organic Chemistry or Chemistry of the Carbon Compounds. vol. 1. Philadelphia, Pennsylvania, U.S.A.: P. Blakiston's Son & Co. p. 466. |volume= has extra text (help)
^Munegumi, Toratane (23 January 2013). "Where is the Border Line between Strong Acids and Weak Acids?". World Journal of Chemical Education. 1 (1): 12–16.
^Martell, A. E.; Smith, R. M.; Motelaitis, R. J. (2001). NIST Database 46. Gaithersburg, MD: National Institute of Standards and Technology.
^Wierzejewska, M.; Mielke, Z. (2001). "Photolysis of Isothiocyanic Acid HNCS in Low-Temperature Matrices. Infrared Detection of HSCN and HSNC Isomers". Chemical Physics Letters. 349 (3–4): 227–234. Bibcode:2001CPL...349..227W. doi:10.1016/S0009-2614(01)01180-0.
^ . Barakat, T. M.; Nelson, J.; Nelson, S. M.; Pullin, A. D. E. (1969.) “Spectra and hydrogen-bonding of characteristics of thiocyanic acid. Part 4.—Association with weak proton acceptors”. Trans. Faraday Soc., 1969,65, 41-51