Rotational auto-detachment of acetonitrile, trimethyl-acetonitrile, acetone, and cyclobutanone dipole bound anions was studied under varying conditions in a Rydberg electron transfer (RET) time-of-flight apparatus. Varying amounts of auto-detachment was observed for anions with similar electron affinity and dipole moment, but different moments of inertia. These results were found to be consistent with predictions based on the calculated rotational spectra for these anions, highlighting the importance of critical binding properties in understanding the stability and lifetime of dipole bound systems. (C) 2016 Elsevier B.V. All rights reserved.