In this study, we analyze the populations of phenol clusters in solution through atomistic simulations, extending our analysis to tetramers. The two developed strategies are applied to compute the populations of phenol aggregates, which are eventually used to simulate the average IR spectra at varying phenol/CCl 4 ratios, focusing on the challenging O H broadband. Our results offer valuable insights into the strengths and limitations of both approaches in capturing enthalpic and entropic contributions to aggregate formation. This paper is organized as follows: Section 2 provides a detailed description of the newly developed approaches for determining aggregate populations and outlines the method for calculating averaged IR spectra. Section 3 presents the computational details. Section 4 discusses the main findings, and the conclusions are presented in Section 5.