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Assuming we have some harmonic oscillator \begin{equation} H = \omega_0 (a^\dagger a + \frac{1}{2}) = \frac{p^2}{2m} + k x^2 \end{equation} for which the excitations have even wavefunctions $\Psi_n(x)=\langle x\vert (a^\dagger)^n \vert 0 \rangle$. The momentum and position operators can be expressed as differences/sums of the creation and annihilation operators i.e. $x \propto (a^\dagger + a)$. Upon minimal coupling to light $p\rightarrow p - e A$, we can consider the scattering amplitudes for IR, Raman and Reyleigh scattering, which can be derived via perturbation theory (see e.g. Louisell: Quantum Statistical Properties of Radiation).

In particular the Raman amplitude for scattering from $\vert n_i\rangle$ to $\vert n_f \rangle$ will have a numerator \begin{equation} \sum_{I=0}^\infty\langle n_f \vert \mu \vert n_I \rangle \langle n_I \vert \mu \vert n_i \rangle \end{equation} where $\mu= ex$ is the dipole operator. But due to the linearity of $x$ in $a$ and $a^\dagger$, $n_I$ gets restricted to $n_I = n_i\pm 1$ and therefore also $n_f$ gets restricted, namely to $n_f = n_i$ or $n_f = n_i \pm 2$. But the case $n_f = n_i$ means that the scattering was elastic hence Reyleigh scattering not Raman. Whereas $n_f = n_i \pm 2$ seems like it would correspond to a second order IR absorbtion(+) or emission (-). The second point is not entirely clear, because a priori I could also have a Stokes(+) or Anti-Stokes(-) Raman process ending in these states. However, at least in my mind, a Raman process requires a virtual state that absorbs the entire incoming photon i.e. significantly (more than 1 level) above the initial state so it can decay to a higher/lower energy final state and emit a photon with lower/higher energy. In the HO case the overlap to virtual states with energy more than 1 level removed from the initial state vanishes.

Am I correct in my deduction that a single harmonic oscillator even if it was Raman active from a symmetry perspective cannot Raman-scatter?

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Let me answer my own question based on the information I found in Chem. Rev. 1994, 94, 157-193 and PRL 119, 127402 (2017).

The way I formulated the coupling of the HO to light, it would indeed not be able to Raman scatter in the classical meaning of the word. Though I have found that Sum-Frequency Raman scattering (SF-RS) is a word (ab)used for the 2nd order absorbtion/emission that is possible in the system.

However, my Hamiltonian was a bit too simplistic. The model that is used in the literature for simple Raman scattering off of a single phonon mode for example uses the interaction term \begin{equation} \textbf{P}(X,\textbf{E})\cdot \textbf{E} \end{equation} with the polarization $\textbf{P}$ dependent on both the HO coordinate ,$X$, and the electric field $\textbf{E}$. It can be expanded as a power series in the electric field \begin{equation} P_i(X,\textbf{E}) = P^{(0)}_i(X) + \chi_{ij}(X)E_j + O(E^2) \end{equation} Now the force appearing in the equations of motion will be \begin{equation} \frac{\partial P(X,\textbf{E})}{\partial X}\cdot\textbf{E} \end{equation} If the system is centrosymmetric the normal mode $X$ belongs either to an even(gerade) or odd(ungerade) representation of the symmetry group. The zero order term is clearly spatially odd while the electric susceptibility, $\chi$ is even. Since the Hamiltonian commutes with the symmetry operation the different irreps don't mix and $\textbf{P}^{(0)}$ can only be influenced by an odd $X$, while $\chi$ can only be influenced by an even $X$. Because of this, either $\partial_X P^{(0)}=0$ or $\partial_X \chi_{ij} = 0$, corresponding to the rule of mutual exclusion (since the first term is linear in $\textbf{E}$ so IR active and the second is quadratic so Raman active).

Essentially, the oversimplification I made was to think that $X$ would couple directly to light. In reality, the actual coupling is more complicated involving the electrons and ions of the atoms involved in the phonon. This is represented by the function $\textbf{P}(X,\textbf{E})$ which is not just linear in X and therefore avoids the restriction I concluded in my question.

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