title: A colorimetric proton sponge.
abstract: 1,8-Bis(dimethylamino)naphthalene ("Proton Sponge") and bromomaleic anhydride react quickly at room temperature, generating 3-(4,5-bis(dimethylamino)napthalen-1-yl)furan-2,5-dione (4-maleicanhydridoproton sponge or "MAPS"). MAPS is a deep purple solid that exhibits positive solvatochromism in solution. It is a weaker base than Proton Sponge. When protonated in solution, MAPS loses its color, but the color change can be reversed by deprotonation with a stronger base. MAPS thus acts as a colorimetric version of a proton sponge.
authors.affiliation: Department of Chemistry, University of Oregon, Eugene, Oregon 97403, USA.
authors.forename: Charles D
authors.initials: CD
authors.lastname: Swor
authors.forename: Lev N
authors.initials: LN
authors.lastname: Zakharov
authors.forename: David R
authors.initials: DR
authors.lastname: Tyler
mesh_terms: D015057:1-Naphthylamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D003124:Colorimetry; D018360:Crystallography, X-Ray; D008299:Maleic Anhydrides / Q000138:chemical synthesis* / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D011522:Protons; D013237:Stereoisomerism
chemical_list: C555282:3-(4,5-bis(dimethylamino)napthalen-1-yl)furan-2,5-dione; D008299:Maleic Anhydrides; D011522:Protons; C555283:bromomaleic anhydride; C418992:1,8-bis(dimethylamino)naphthalene; D015057:1-Naphthylamine