Semicarbazone

In organic chemistry, a semicarbazone is a derivative of imines formed by a condensation reaction between a ketone or aldehyde and semicarbazide. They are classified as imine derivatives because they are formed from the reaction of an aldehyde or ketone with the terminal -NH2 group of semicarbazide, which behaves very similarly to primary amines.

General chemical structure of a semicarbazone
Nitrofurazone is a semicarbazone used as an antiseptic

Formation
For ketones
H2NNHC(=O)NH2 + RC(=O)R → R2C=NNHC(=O)NH2
For aldehydes
H2NNHC(=O)NH2 + RCHO → RCH=NNHC(=O)NH2

For example, the semicarbazone of acetone would have the structure (CH3)2C=NNHC(=O)NH2.

Properties and uses

Some semicarbazones, such as nitrofurazone, and thiosemicarbazones are known to have anti-viral and anti-cancer activity, usually mediated through binding to copper or iron in cells. Many semicarbazones are crystalline solids, useful for the identification of the parent aldehydes/ketones by melting point analysis.[1]

A thiosemicarbazone is an analog of a semicarbazone which contains a sulfur atom in place of the oxygen atom.

gollark: It's browser-dependent. Probably in a database in the browser's app data folders somewhere.
gollark: Put a textarea in the HTML part of your thing, and some buttons to save/~~edit~~/delete etc. Those can read the `value` property of it and save it to localstorage (you should also read its contents and set the value to that on page load).
gollark: Yes, you can also read localstorage, it would not be useful otherwise.
gollark: Java and JS aren't the same. Anyway, the page has some examples for writing to it.
gollark: https://developer.mozilla.org/en-US/docs/Web/API/Window/localStorage

See also


References
  1. Williamson, Kenneth L. (1999). Macroscale and Microscale Organic Experiments, 3rd ed. Boston: Houghton-Mifflin. pp. 426–7. ISBN 0-395-90220-7.
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