Isothiocyanate
In organic chemistry, isothiocyanate is a functional group as found in compounds with the formula R−N=C=S. Isothiocyanates are the more common isomers of thiocyanates, which have the formula R−S−C≡N.
Occurrence
Many isothiocyanates from plants are produced by
Structure
The N=C and C=S distances are 117 and 158
Typical
Synthesis
Allyl thiocyanate isomerizes to the isothiocyanate:[4]
- CH2=CHCH2SCN → CH2=CHCH2NCS
Isothiocyanates can be prepared by degradation of
Isothiocyanates may also be accessed by the fragmentation reactions of 1,4,2-oxathiazoles.[7] This methodology has been applied to a polymer-supported synthesis of isothiocyanates.[8]
Reactions
Isothiocyanates are weak electrophiles, susceptible to hydrolysis. In general, nucleophiles attack at carbon:
Flavor research
Isothiocyanates occur widely in nature and are of interest in food science and medical research.[1] Vegetable foods with characteristic flavors due to isothiocyanates include bok choy, broccoli, cabbage, cauliflower, kale, wasabi, horseradish, mustard, radish, Brussels sprouts, watercress, papaya seeds, nasturtiums, and capers.[1] These species generate isothiocyanates in different proportions, and so have different, but recognizably related, flavors. They are all members of the order Brassicales, which is characterized by the production of glucosinolates, and of the enzyme myrosinase, which acts on glucosinolates to release isothiocyanates.[1]
- Sinigrin is the precursor to allyl isothiocyanate
- Glucotropaeolin is the precursor to benzyl isothiocyanate
- Gluconasturtiin is the precursor to phenethyl isothiocyanate
- Glucoraphanin is the precursor to sulforaphane
Uses
Phenyl isothiocyanate, is used for amino acid sequencing in the Edman degradation.
Coordination chemistry
Isothiocyanate and its
See also
References
- ^ a b c d "Isothiocyanates". Micronutrient Information Center, Linus Pauling Institute, Oregon State University. 1 April 2017. Retrieved 14 April 2019.
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- PMID 17444687.
- PMID 19245242.
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