earticle

영어

To understand on the hydrolysis reactivity of 2-chlorobenzylidenemalononitrile (S) molecule as riot control agent and chronic (or acute) toxicity of hydrolysis products, MO (Molecular orbital) calculation by MOPAC AM1 method, toxicity predictions by ADME and TOPKAT were performed and discussed quantitatively. The most stable stereo conformer of the molecule (S) was antiperiplanar (θ o = 48, E = 3.7378 ev.) form, and the calculated MO functions were εHOMO= −10.0422 ev. and εLUMO = −0.9215 ev., respectively. Therefore, from FMO (Frontier molecular orbital) interactions, it is showed that the nucleophilic addition (A) and electrophilic addition (B) reactions occurs (A ≤ B) competitively. In the neutral, hydrolysis of the molecule (S) proceeds through an nucleophilic addition-elimination (AdNu-E) and hydrolysis products were 2-chlorobenzaldehyde and malononitrile. Based on the predicted toxicity by ADME and TOPKAT, generally, it was shown that malononitrile had higher tendency than the molecule (S).

한국어

시위 진압용 최루성 물질인 2-chlorobenzylidenemalononitrile 분자(S)의 가수분해 반응성과 급만성 독성을 이해하고자, MOPAC AM1 방법으로 MO함수를 계산하고, ADME 및 TOPKAT 방법으로 독성예측을 실행하고 검토하였다. 가장 안정한 입체 형태는 antiperiplanar (θ ο= 48 및 E = 3.7378 ev.) 형이었고 MO함수의 에너지(ev.)는 εHOMO: −10.0422 ev. 및 εLUMO: −0.9215 ev.이었다. 경계궤도함수(FMO:Frontier molecular orbital) 상호작용으로부터 친핵성 첨가반응(A)과 친전자성 첨가반응(B)이 경쟁적으로(AB) 일어남을 나타내었다. 또한, 중성에서는 친핵성 첨가-제거반응(AdNu-E) 메카니즘으로 가수분해반응이 일어나며 분해 생성물은 2-chlorobenzaldehyde 및 malononitrile이었다. ADME 및 TOPKAT에 의한 독성 예측결과, 대체로 분자(S)보다 malononitrile이 높은 독성을 나타내는 경향이었다.