It is known that the specific heat of a gas is process dependent.So it must be theoretically possible to have a negative value for a gas according to the following equation (for polytropic process): $$ C = \frac R{\gamma-1} + \frac R{1-n} $$ where $C$ is molar specific heat and $\gamma$ is adiabatic exponent.
(supposing $\gamma = \frac{5}{3}$ and $n = \frac{4}{3}$, $C$ comes out to be negative)
Is it practically possible and if so what would it signify? As you provide more heat to a gas in such a process, would it lose temperature? Please clarify.