In this study, we perform an MPW1K investigation on the kinetic stability of a cyclic boryl anion. According to our calculation, the bulkier the R and R’ groups are, the more kinetically stable a five-membered boryl anion may be. Nitrogen should be a more efficient π donor to increase the kinetic stability of a cyclic boryl anion than P, As, O, S and Se. Although, one nitrogen atom is enough to stabilize a cyclic boryl anion from the kinetic aspect, the stability of a cyclic
boryl anion increases as the number of nitrogen in the ring increases. The six-membered boryl anion is calculated to be more stable kinetically than the five-membered one that has been synthesized successfully.