Synthesis, characterization and phytotoxic activity of hydroxylated isobenzofuran-1(3H)-ones R.R. Teixeira a,⇑ , J.L. Pereira a , S.F. Da Silva a , S. Guilardi b,⇑ , D.A. Paixão b , C.P.A. Anconi c , W.B. De Almeida d , J. Ellena e , G. Forlani f a Departmento de Química, Universidade Federal de Viçosa, Viçosa, Minas Gerais, Brazil b Instituto de Química, Universidade Federal de Uberlândia, Uberlândia, Minas Gerais, Brazil c Departamento de Química, Universidade Federal de Lavras, Lavras, Minas Gerais, Brazil d Departamento de Química, Instituto de Ciências Exatas, Universidade Federal de Minas Gerais, Belo Horizonte, Minas Gerais, Brazil e Instituto de Física de São Carlos, Universidade de São Paulo, São Carlos, SP, Brazil f Department of Life Science and Biotechnology, University of Ferrara, Ferrara, Italy highlights  Compounds 3 and 4 crystallized in the space group Pc and P2 1 /n, respectively.  DFT calculations confirmed undoubtedly their NMR chemical shifts.  A good agreement was also obtained for B3LYP/6-31G(d,p) theoretical and experimental IR spectra.  Isobenzofuran-1(3H)-ones 3 and 4 interfere with the radicle growth of monocotyledonous and dicotyledonous species. graphical abstract HO O O 3 O O 4 HO article info Article history: Received 17 September 2013 Received in revised form 17 December 2013 Accepted 18 December 2013 Available online 2 January 2014 Keywords: Isobenzofuran-1(3H)-ones Phthalides X-ray analysis DFT calculations Phytotoxicity abstract Two hydroxylated isobenzofuranones 3 and 4 were synthesized from benzoic acids. The compounds were fully characterized by IR, NMR ( 1 H and 13 C), HRMS, and X-ray crystallography. Compounds 3 and 4 crystallized in the space group Pc and P2 1 /n, respectively. DFT calculations were used to confirm undoubtedly their NMR chemical shifts. Biological assays showed that these compounds are capable of interfering with the radicle growth of monocotyledonous and dicotyledonous species, whereas the photosynthetic electron transport chain was substantially unaffected. Ó 2013 Elsevier B.V. All rights reserved. 1. Introduction Several natural and synthetic compounds possess a c-butirolac- tone fused to a benzene ring. These substances, known as isobenzofuran-1(3H)-ones (phthalides), have attracted attention of various research groups due to their wide range of medicinal 0022-2860/$ - see front matter Ó 2013 Elsevier B.V. All rights reserved. http://dx.doi.org/10.1016/j.molstruc.2013.12.059 ⇑ Corresponding authors. Tel.: +55 31 3899 3209/34 3239 4444; fax: +55 31 3899 3065/34 3239 4208. E-mail addresses: robsonr.teixeira@ufv.br (R.R. Teixeira), silvana@ufu.br (S. Guilardi). Journal of Molecular Structure 1061 (2014) 61–68 Contents lists available at ScienceDirect Journal of Molecular Structure journal homepage: www.elsevier.com/locate/molstruc