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Description of key information

At ambient conditions amines are stable in aqueous surroundings.

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Additional information

In amines the bond between the terminal (saturated) carbon atom and the nitrogen atom (single bond) is polarized with a positive partial charge at the carbon atom. The enthalpy of the C-N bond is 291.8 kJ/mol. This is less than the binding enthalpy of the C-O bond in alcohols. In this bond the carbon atom is sp3 hybridized. The formal oxidation number is + I. The positively charged carbon atom is in principle capable to undergo nucleophilic substitution with an electron rich species (for example strong bases). Water exhibits nucleophilic properties, but it is not a strong enough nucleophile to generate an efficient reaction with amines under am-bient conditions. The energy barrier for the nucleophilic substitution reaction is too high to be overcome. Thus there is no hydrolytic degradation of amines in aqueous environmental compartments under ambient conditions.