Lithium phenolates solvated by tetrahydrofuran and 1,2-dimethoxyethane: structure determination using the method of continuous variation.
The method of continuous variation in conjunction with (6)Li NMR spectroscopy was used to characterize lithium phenolates solvated by tetrahydrofuran and 1,2-dimethoxyethane. The strategy relies on the formation of ensembles of homo- and heteroaggregated phenolates. The symmetries and concentration dependencies of the heteroaggregates attest to the aggregation numbers of the homoaggregates. The structurally diverse phenols afford substrate- and solvent-dependent combinations of lithium phenolate monomers, dimers, trimers, tetramers, and pentamers. We discuss the refinement of protocols for characterizing O-lithiated species. Computational studies examine further the substituent and solvent dependencies of aggregation.
De Vries
Timothy S
TS
Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University, Ithaca, New York 14853-1301, USA.
Goswami
Anandarup
A
Liou
Lara R
LR
Gruver
Jocelyn M
JM
Jayne
Emily
E
Collum
David B
DB
D005019:Ethyl Ethers / Q000737:chemistry; D005663:Furans / Q000737:chemistry; D008094:Lithium / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D010636:Phenols / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry
D005019:Ethyl Ethers; D005663:Furans; D010636:Phenols; D012997:Solvents; C018674:tetrahydrofuran; D008094:Lithium; C024683:1,2-dimethoxyethane
Chem Rev. 2006 Jul;106(7):2596-616
16836294
Org Lett. 2002 Feb 21;4(4):573-5
11843594
Dalton Trans. 2006 Apr 21;(15):1875-84
16585975
J Am Chem Soc. 2004 May 19;126(19):5938-9
15137738
Angew Chem Int Ed Engl. 2000 May 15;39(10):1823-1826
10934375
Angew Chem Int Ed Engl. 2006 Nov 20;45(45):7506-25
17103481
Angew Chem Int Ed Engl. 1999 Nov 15;38(22):3367-3370
10602197
J Am Chem Soc. 2003 Nov 26;125(47):14411-24
14624589
Angew Chem Int Ed Engl. 2000 Apr;39(8):1467-1470
10777644
J Am Chem Soc. 2008 Apr 9;130(14):4859-68
18336025
J Org Chem. 2008 Oct 3;73(19):7743-7
18781812
J Org Chem. 2003 Apr 4;68(7):2830-8
12662059
Dalton Trans. 2006 Jul 21;(27):3338-49
16820846
Angew Chem Int Ed Engl. 2008;47(30):5650-3
18567044
Magn Reson Imaging. 2000 Feb;18(2):103-16
10722969
Inorg Chem. 2000 Oct 30;39(22):5133-46
11233212
J Am Chem Soc. 1988 Aug 1;110(18):6058-63
22148781
Inorg Chem. 2007 Oct 29;46(22):9379-88
17880064
Methods Enzymol. 1982;87:509-25
7176926
J Am Chem Soc. 2001 Jul 11;123(27):6527-35
11439039
J Org Chem. 1999 May 14;64(10):3390-3391
11674455
J Org Chem. 2001 Dec 28;66(26):9005-10
11749634
J Am Chem Soc. 2006 Jul 26;128(29):9355-60
16848470
Acc Chem Res. 2009 Feb 17;42(2):270-80
19105594
Angew Chem Int Ed Engl. 2004 May 24;43(22):2965-7
15170317
Chem Rev. 2006 Jul;106(7):2734-93
16836298
J Am Chem Soc. 2004 Dec 22;126(50):16559-68
15600361
J Am Chem Soc. 2005 Apr 6;127(13):4965-75
15796563
Org Lett. 1999 Jul 15;1(1):145-7
10822549
J Am Chem Soc. 2006 Aug 9;128(31):10326-36
16881665
J Org Chem. 2006 May 26;71(11):4031-9
16709041
J Am Chem Soc. 2007 Oct 3;129(39):12023-31
17850084
J Am Chem Soc. 2002 Jan 16;124(2):264-71
11782178
J Org Chem. 2008 Dec 5;73(23):9393-402
18954115
J Am Chem Soc. 2005 Apr 20;127(15):5655-61
15826205
J Am Chem Soc. 2003 Dec 17;125(50):15376-87
14664582
J Am Chem Soc. 2008 Oct 29;130(43):14179-88
18828636
Angew Chem Int Ed Engl. 2007;46(28):5314-6
17579905
Angew Chem Int Ed Engl. 2005 Feb 25;44(10):1448-54
15724254
Org Lett. 2001 Aug 9;3(16):2599-601
11483070
J Am Chem Soc. 2008 Dec 24;130(51):17334-41
19090750
J Mol Model. 2006 Jul;12(5):673-80
16341718
J Org Chem. 2008 Aug 15;73(16):6086-91
18646860
J Am Chem Soc. 2001 Aug 22;123(33):8067-79
11506563
J Org Chem. 1996 Jul 12;61(14):4589-4593
11667384