Subject: [Fwd: PACK of replies: DFT/H-bonds]

From: Didier MATHIEU <[email-masked]>
Date: Fri, 29 Jan 1999 16:02:11 +0000

[Edited by CCL Administrator -- long headers and repeats removed

Dear all,
In reply to requests, here are the replies I got to my question about
DFT description of H-bonds.
Regards
-- 
Didier MATHIEU
CEA - Le Ripault, BP 16
37260 Monts (France)
Tel. 33(0)2.47.34.41.85

Here are the replies I got to my answer.

-- 
Didier MATHIEU
CEA - Le Ripault, BP 16
37260 Monts (France)
Tel. 33(0)2.47.34.41.85

--------------
Subject:
Date: Mon, 25 Jan 1999 10:17:27 -0600 (CST)
From: Carlo Adamo <[email-masked]>
To: [email-masked]

Ciao Didier,

I did some works about DFT & H-bond. Please give a look at these papers:

Chem. Phys. Lett. 224 (1994) 432
Chem. Phys. Lett. 231 (1994) 295
J. Chem. Phys. 102 (1995) 364
Int. J. Quantum. Chem. 56 (1995) 697
J. Phys. Chem.  99 (1995) 15062
J. Chem. Phys. 105 (1996) 11007
Int. J. Quantum. Chem. 61 (1997) 429
J. Comp. Chem.  18 (1997) 1993

a review was published in:
Recent Advances in Density Functional Methods, Part II, Edited by
D.P. Chong, World Scientific Press, Singapore (1997).

Furthermore the computation of H-bond strength in small complexes, as
water dimer, is one of the tests to check the performances of
new functionals. So you might find some informations also in

J. Chem. Phys. 108 (1998) 664
J. Comp. Chem.  19 (1998) 418

Carlo

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--------------
>From [email-masked]  Tue Jan 26 16:03:35 1999
Date: Tue, 26 Jan 1999 09:59:46 -0500
From: Andrew T Pudzianowski <[email-masked]>
Subject: Re: CCL:Hydrogen Bonds with DFT / GGA
To: Didier MATHIEU <[email-masked]>

Didier MATHIEU wrote:
> 
> Hello everybody,
> 
> I have carried out some calculations of energetic data for molecules
> including nitroaromatics with gradient-corrected DFT functionals,
> especially Becke-Perdew86.
> The results are satisfactory excepted for tri-amino-trinitro-benzene,
> the only molecule in my dataset showing intramolecular hydrogen bond.
> I read somewhere that DFT was not very good at describing hydrogen
> bonds.
> I wonder if anybody can provide me some details about this subject, i.e.
> performance of DFT with regard to hydrogen bonds.
> 
> Thank you.
> Regards
> 
> --
> Didier MATHIEU
> CEA - Le Ripault, BP 16
> 37260 Monts (France)
> Tel. 33(0)2.47.34.41.85
> 
> -------This is added Automatically by the Software--------
> -- Original Sender Envelope Address: [email-masked]
> -- Original Sender From: Address: [email-masked]
> [email-masked]: Everybody | [email-masked]: Coordinator
> [email-masked]: HELP CHEMISTRY or HELP SEARCH | Gopher: www.ccl.net 73
> Anon. ftp: www.ccl.net   | [email-masked] -- archive search
>              Web: http://www.ccl.net/chemistry.html
Dear Dr. Mathieu -
    I have done some work myself on this subject. There are two
publications you might find informative, as follows:
A. T. Pudzianowski, "A Systematic Appraisal of Density Functional
Methodologies for Hydrogen Bonding in Binary Ionic Complexes," J. Phys.
Chem. 100, 4781-4789 (1996)
A. T. Pudzianowski, "Current Computational Approaches to the Strong
Hydrogen Bond," in "Recent Research Developments in Physical Chemistry,"
vol. 1, Transworld Research Network, Trivandrum, India (1997), pp.
81-97.

The second is a review with lots of references; unfortunately, the book
may be hard to find but I can send a reprint if you wish. Both of these
can serve as an effective introduction to the subject and the newer
literature.

                     With best wishes,
                     Andrew Pudzianowski

>From [email-masked]  Tue Jan 26 09:35:20 1999
Date: Tue, 26 Jan 1999 10:33:38 +0000
From: Isabel Rozas <[email-masked]>
Subject: HB with DFT
To: [email-masked]

Hello there!
I don't know if you remember me, it was many many years ago that 
we met in some of this french-spanish conferences. I did my PhD
with Pilar Goya and now I work with her and with Prof. Elguero 
in Madrid in the Medicinal Chemistry Institute.
I am also subscribe to the computational chemistry list so I saw
your question this morning. Enough of presentations and let's go
with the question. 
Latetly we have work quite a lot in hydrogen bonding. We have used
from HF/6-31G till MP2 (and more)/6-311++G**. Also we have used
DFT but not the Becke-Perdew86 but the B3LYP. I do not too much 
about the Perdew but I can tell you that the Becke3LYP works
very well for hydrogen bonds. We have even found out that using
B3LYP/6-311++G** (or even with a little smaller base like 6-31+G*)
you get results similar to those obtained with MP2/6-311++G**.
Some of our work is gathered in: 
	I. Alkorta, I. Rozas and J. Elguero.
	"Non-conventional hydrogen bonds"
	Chem. Soc. Rev., 163-170, 27 (1998).
but if you want more information we have just create a web page
with all the theoretical work we are doing and maybe can be
of some utility for you. The address of that web page is as follows:
http://www.iqm.csic.es/are/main.htm
So trying to answer your question, I don't beleive is a problem of DFT
but maybe can be a problem of the method you chose (BeckePerdew86 vs.
Becke3LYP). I do not know either which program are you using byt this
B3LYP is included in Gaussian94 and 98.
I hope everything is fine with you and I sent you my regards

Isabel Rozas

>From [email-masked]  Tue Jan 26 10:18:48 1999
From: "Jens Spanget-Larsen" <[email-masked]>
To: Didier MATHIEU <[email-masked]>
Date: Tue, 26 Jan 1999 10:21:49 +0100
Subject: Re: CCL:Hydrogen Bonds with DFT / GGA

Didier MATHIEU:

> I have carried out some calculations of energetic data for molecules
> including nitroaromatics with gradient-corrected DFT functionals,
> especially Becke-Perdew86. 
> The results are satisfactory excepted for tri-amino-trinitro-benzene,
> the only molecule in my dataset showing intramolecular hydrogen bond.
> I read somewhere that DFT was not very good at describing hydrogen
> bonds.
> I wonder if anybody can provide me some details about this subject, i.e.
> performance of DFT with regard to hydrogen bonds.

We obtained satisfactory results with B3LYP/6-31G* for molecular and 
vibrational structures of intramolecularly H-bonded beta-hydroxy 
carbonyl compounds like malonaldehyde enol and anthralin:

Chem. Phys. 240, 51-61 (1999)
J. Mol. Struct. 475, 131-140 (1999)

Yours, Jens >--<
                             
=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=
JENS SPANGET-LARSEN         Phone:  +45 4674 2000  (RUC)
Department of Chemistry             +45 4674 2710  (direct)
Roskilde University (RUC)   Fax:    +45 4674 3011 
P.O.Box 260                 E-Mail: [email-masked]
DK-4000 Roskilde, Denmark   http://www.rub.ruc.dk/dis/chem/psos/
=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=

>From [email-masked]  Tue Jan 26 09:09:35 1999
From: Michael Braeuer <[email-masked]>
Subject: Re: CCL:Hydrogen Bonds with DFT / GGA
To: [email-masked] (Didier MATHIEU)
Date: Tue, 26 Jan 99 9:13:41 MET

> 
> Hello everybody,
> 
> I have carried out some calculations of energetic data for molecules
> including nitroaromatics with gradient-corrected DFT functionals,
> especially Becke-Perdew86. 
> The results are satisfactory excepted for tri-amino-trinitro-benzene,
> the only molecule in my dataset showing intramolecular hydrogen bond.
> I read somewhere that DFT was not very good at describing hydrogen
> bonds.
> I wonder if anybody can provide me some details about this subject, i.e.
> performance of DFT with regard to hydrogen bonds.

Hi,

the Montreal group around Prof. Salahub developed a functional called
LAP3 which is able to handle hydrogen bonds correctly (even transition
states for hydrogen transfer). This work is conected mainly to
E. Proynov after whom the functional is named.

If you contact them they surely provide you with their program DeMon.

Best regards

Michael

--
Michael Braeuer           http://www.uni-jena.de/chemie/anders/micha.htm
PhD Student               E-mail: [email-masked]
IOMC FSU Jena             Tel:     ++49/3641/948217
Humboldtstrasse 10        Fax:     ++49/3641/948212
07743 Jena
Germany

>From [email-masked]  Mon Jan 25 23:06:59 1999
Date: Mon, 25 Jan 1999 23:07:14 +0100 (MEZ)
From: Elmar Gerwalin <[email-masked]>
To: [email-masked]
Subject: Second (and last) list of articles

Hi Didier
Here comes the second (and last) list of articles I have about
H-bonded systems. It#s from Thomas Steiner from Berlin, who does
crystallisation experiments and is not a theretical chemist.
Hope that helps you, nevertheless.

Bye
Elmar
(the part from the original mail, that was in german:)
  Umezawa et al., Bull.Chem.Soc.Jpn, 71, 1998, 1207.
Uebersichtsartikel: Nishio et al., Tetrahedron, 51, 1989, 7201 und
  Tetrahedron, 51, 1995, 8665.

for organic chemists mainly (collections of structures from databases)

(a book:) M.Nishio, M.Hirota and Y. Umezawa. The CH/pi interaction. Evidence, nature
 and consequences. Wiley, New York, 1998.

Ich selbst habe ueber CH-pi mit aciden CH Gruppen publiziert, z.B.
Steiner et al., Acta Cryst. B53, 1997, 843, J.Chem.Soc., Perkin Trans, 2,
1995, 1312 und 1996, 2441. 

Theoretical articles !:
Rozas et al., J.Phys.Chem.A, 101, 1997, 9457,
Review: Alkorta et al., Chem.Soc.Rev., 27, 1998, 163.

(author:Thomas Steiner , Berlin)

>From [email-masked]  Mon Jan 25 22:56:46 1999
From: Dmitry Khoroshun <[email-masked]>
Subject: Re: CCL:Hydrogen Bonds with DFT / GGA
To: [email-masked] (Didier MATHIEU)
Date: Mon, 25 Jan 1999 16:56:47 -0500 (EST)

Hello!

Some people think that the quality of description of hydrogen bonds by
density functional methods is very sensitive to the quality of the basis
set used. One of the suggestions is that the convergence of DFT methods
with respect to basis set is much slower than that of, for example, MP2.

You may want to check

CPL 1995, 245, 129
CPL 1995, 247, 112
Canadian J. Chem. 1995, 73, 710
JPC 1995, 99, 5899
JPC 1995, 99, 15837
JPC 1996, 100, 3942

Usually, gradient-corrected functionals are reliable with large basis sets

CPL 1996, 254, 135
CPL 1996, 263, 345
JPC 1995, 99, 592

Sincerely,
Dmitry Khoroshun
[email-masked]

>From [email-masked]  Mon Jan 25 22:55:19 1999
Date: Mon, 25 Jan 1999 22:55:18 +0100 (MEZ)
From: Elmar Gerwalin <[email-masked]>
To: [email-masked]
Subject: List of articles on DFT+HBOND

Hi Didier
Here's the first list of articles I found on your theme.
It's  a summary from the CCL from a while ago: Hope it helps.

>From chemie.uni-kl.de!elg Mon Jan 25 22:50:14 1999
Date: Mon, 25 Jan 1999 22:50:11 +0100
From: [email-masked] (Elmar Gerwalin)
To: gerwalin@rhrk

>From [email-masked]  Wed Aug 13 21:35:52 1997
Date: Wed, 13 Aug 1997 14:09:07 -0400 (EDT)
From: Anatoli Korkin <[email-masked]>
Subject: CCL:G:Summary - B3LYP for H-bonded systems
To: [email-masked]

>Does any one know references on comparative ab initio and DFT (preferably 
>B3LYP) studies of H-bonded systems and proton transfer? Any reviews on
>this topic?

Dear CCLers,
CCLers,

Thanks to everybody who responded on my question. I have received as
much answers as requests for summary. It was also fun to hear from and
about my old friends and to make new contacts. H-boding seems to be a
nice topic for a chat, although I was surprized it is still so popular :-)

We have decided to extend our introduction a bit to cite and to discuss
some recent results.

Have a good day, everybody!

Anatoli

P.S. Sorry, I have no time to clean up messages properly. Please, substract 
what you need yourself. I also keep the addresses to let H-bonding community 
to have some local talks among them :-)

Summary:
--------

Dear Anatoli,

Dennis Salahub has worked on this extensively; several imporatant papers
were published recently, also with repsect to developing new functionals
for these purposes (BLap.. functionals).

What systems are you interested in? Please summarize the responses,
I'm curious.

Hope all is well at your end. It's finally HOT here (for German standards).

All the best,
Peter

-- 

    ////
___|--00___________________________________________________________________
   C   ^     Dr. Peter R. Schreiner
    \ ~/     Institut fuer Organische Chemie
    <><>     Georg-August Universitaet Goettingen
             Tammannstr. 2                    Phone: +49-(0)551-393287
             D-37077 Goettingen, Germany      FAX:   +49-(0)551-399475
	     http://www.gwdg.de/~ucoc/schreiner
___________________________________________________________________________

HI, ANATOLI -

     I can certainly give you one.
J. E. Del Bene, W. B. Person, and K. Szczepaniak,
J. Phys. Chem. 99, 10705 (1995).

     DFT/B3LYP can be quite erratic.  What's up?????   Janet

hi Anatoli, 

I've been working for a while in H-bonded systems comparing dft (b3lyp is
included) and ab-initio methods. 
Maybe this can help:

"Cooperative effects in water trimers. The performance of density
functional approaches" L. Gonzalez et al.  J. Molec. Struct. (Theochem)
371 (1996) 1

"High level ab initio versus DFT calculations on (H2O2)2 and H2O2-H2O
complexes as prototypes of multiple h-bonded systems" L. Gonzalez et al. 
J. Comput. Chem. 18 (1997) 1124.

Best wishes, 

	Leticia Gonzalez
*********************************
*  Leticia Gonzalez             *
*  Dept. of Chemistry           *
*  Dalhousie University         *
*  Halifax, NS  B3H 4J3         *
*  Canada                       *
*                               *
*  Phone:   902-494 7021        *
*  e-mail: [email-masked]   *
*********************************

Hi Anatoli,

I assumed you already received a message from Leti Gonzales about her 
work done on water dimers (she sits next door in Boyd's lab).

I also can add to that list a paper J.Chem.Soc., Faraday Trans., 
1997, 93(2), 333.

Best regards,

Vladimir

**********************************************************************
Vladimir V. Murashov                 

Department of Chemistry                  tel   : +1-902-494-6538
Dalhousie University                     fax   : +1-902-494-1310
Halifax, NS                              E-mail: [email-masked]
Canada B3H 4J3
**********************************************************************

I hope you find the following references useful.

Sim et al. JACS 1992, 114, 4391 "Gaussian density functional calculations on h 
bonded systems"

Kovacs et al J. Comp. Chem. 1996, 17(16), 1804 "Theoretical study of 
intramolecular hydrogen bonding ... "

Gonzalez et al J. Comp. Chem. 1997, 18, 1124 " High level ab initio versus dft 
calculations on ... "

Hobza et al J. Comp. Chem. 1995, 16(11), 1315 " density functional theory and 
molecular clusters"

Kind Regards,
Damian Moran

    email: [email-masked]  voice:(+61) 2 9850 8278 
fax:(+61) 2 9850 8313 www:http://www.chem.mq.edu.au/~dmoran
School of Chemistry,Macquarie University,NSW 2109 Australia

H-bonded, i don't know, but you might find

@ARTICLE{Jursic1996a,
        AUTHOR             = {Branko S. Jursic},
        JOURNAL            = CPL,
        PAGES              = {603-608},
        TITLE              = {Density functional theory study of radical 
hydrogen abstraction with hydrogen and hydroxyl radicals},
        VOLUME             = {256},
        YEAR               = {1996}
}

interesting anyway.
---------------------------
Dear Anatoli,

a comparison between HF, MP2, different DFT methods and experimental data 
for the water dimer and hydrogen bonded base pairs is given in:

A. St-Amant, Density functional methods in biomolecular modeling, Reviews 
in Computational Chemistry 7, chapter 5, VCH 1996.

We have carried out some calculations of hydrogen bonded nucleic acid base 
pairs at MP2/6-31G**//HF/6-31G** and B3LYP/6-31G** level. The B3LYP-
intermolecular distances seem to be somewhat better than the HF- 
distances and the interaction energies from single point MP2 and B3LYP 
are in reasonable agreement.

Michael Meyer

-- 
----------------------------------------------------------------------------
Michael Meyer                              
Institut fuer Molekulare Biotechnologie (IMB)     
Biocomputing                                      E-mail: [email-masked]
Beutenbergstrasse 11, Jena                        Tel.:   +49-3641-65-6203
Postfach 100 813, D-07708 Jena, Germany           Fax:    +49-3641-65-6210
----------------------------------------------------------------------------

Anatoli, in response to your question about proton transfer and DFT
methods, we have been doing alot of calcs on the effectiveness of 
various DFT methods for the study of short, strong (or low-barrier)
hyrogen bonds. One of these studies will come out this month in JACS,
watch for it!

If I had to summarize, I would say that in general the B3LYP functional
gives geomtries and energies of reactions almost identical to MP2 in all
cases. BLYP itself often gives hydrogen bond energies a little larger
than either MP2 or B3LYP.  For the hydrogen bifluoride system (coming
out in Theochem shortly) the B3LYP, BLYP, MP2, MP3, MP4, QCISD,and CCSD
results are almost identical. The SVWN and HF results are somewhat 
different than the other correlated methods.

If you are interested in more specifics just contact me.

Mike M.

**************************************************************************
   Michael A. McAllister		
   Assistant Professor of Chemistry	voice: 940-565-4584
   University of North Texas 	 	  fax: 940-565-4318	
   P.O. Box 305070			email: [email-masked]
   Denton, TX 76203			  www: http://people.unt.edu/~mam0008	
**************************************************************************

hese may be of some use:
Proton affinity and DFT  Phys Chem (jpc) 100 (1996) 11595

Deprotonation (E2 reactions) jpc 100 (1996) 16892

Gas-phase acidity            jpc 100 (1996) 17465

C-H...O hydrogen bonds, MP2 cf. B-LYP
                             Chem Phys Letters 266(1,2) (1997) 23
----------

Your friend Igor Svishchev has just joined our Department.

   Best Wishes,

   E. Lewars
=================

Dr. Korkin - 
Forgive me if I recommend a couple of my own publications:
A. T. Pudzianowski, "A Systematic Appraisal of Density Functional
Methodologies for Hydrogen Bonding in Binary Ionic Complexes," 
J. Phys. Chem. 100 (12), 4781-4789 (1996)     and

A. T. Pudzianowski, "Current computational approaches to the strong
hydrogen bond," Recent Res. Devel. in Physical Chem., 1, 81-97 (1997).

The first deals with the strong H-bond and has a lot to say about
comparisons of B3-LYP and B-LYP with MP2, mostly with the 6-311++
G(d,p) basis set. The second is a review of the whole area of com-
putational descriptions of the strong H-bond. The reference is
a bit obscure, so if you're interested please let me know and I'll
send you a reprint.
            Hoping this will be helpful,
             Andrew Pudzianowski
***********************************************************************
Andrew T. Pudzianowski,Ph.D.       
Bristol-Myers Squibb PRI      
Box 4000                  *   "There are two ways to do things.
Princeton NJ 08543-4000   *    There's the scientific way, and               
(609) 252-4248            *    there's the disgusting way."
(609) 252-6030: fax       *          
[email-masked]      *        "Beakman's World", 1994
***********************************************************************

Perhaps

J. M. L. Martin, V. Aviyente, and C. Lifshitz, ``The insertion of amines 
and alcohols into proton bound dimers. A density functional study'', 
Journal of Physical Chemistry A 101, 2597-2606 (1997) 

might interest you.

JM
---------------------------------------------------------------------------
dr. Jan M.L. Martin                Senior Lecturer, Computational Chemistry
       Department of Organic Chemistry/Kimmelman Building, Room 262
            Weizmann Institute of Science/Rechovot 76100/ISRAEL
FAX +972(8)9344142 Phone +972(8)9342533 E-mail [email-masked]
  *** research group WWW home page  http://theochem.weizmann.ac.il/   ***
---- kol ha-olam kulo gesher tzar me'od, v'ha-ikar lo l'hitfached k'lal ---

See for a very recent review :
	
	Carlo Adamo, Vincenzo Barone
	Structural and Dynamical Features of Hydrogen Bonds
	from Conventional and Hybrid Density Functional Methods
	in : Recent Advances in Density Functional Meythods, Part II,
	Ed.: Delano P. Chong, World Scientific, 1997, Chap. 5,
	pp. 115-164
	( Recent Advances in Computational Chemistry, Vol.1 )

-- 
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Hoechst CR&T                    Fax     ++49-69-305-81162                       
Scientific Computing, G864      Email   [email-masked]           
65926 Frankfurt am Main                 [email-masked]

Hi Anatoli,

try

1. P. Hobza, J. Sponer, T. Reschel: "Density Functional Theory and
   Molecular Clusters", J. Comput. Chem. 16 (1995) 1315

2. M. Planas, C. Lee, J. Novoa: "Kinetic of the Proton Transfer in X-(H2O)4
   Clusters (X=H2O, NH3, H2S, and HCl): Evidence for a Concerted Mechanism",
   J. Phys. Chem. 100 (1996) 16495

3. J. Del Bene, W. Person, K. Szczepaniak: "Properties of Hydrogen-Bonded
   Complexes Obtained from the B3LYP Functional with 6-31G(d,p) and 6-31+G(d,p)
   Basis Sets: Comparison with MP2/6-31+G(d,p) Results and Experimental Data",
   J. Phys. Chem. 99 (1995) 10705

4. Z. Latajka, Y. Boutellier, S. Scheiner: "Critical assessment of density
   functional methods for study of proton transfer processes. (FHF)-", Chem.
   Phys. Lett. 234 (1995) 159

5. Z. Latajka, S. Berski: "Density functional study of the H3N-Cl2 system - the
   importance of Hartree-Fock exchange in density function methods", J. Mol.
   Struct. (Theochem) 371 (1996) 11

6. J. Lundell, Z. Latajka: "Density Functional Study of Hydrogen-Bonded Systems:
   The Water-Carbon Monoxide Complex", J. Phys. Chem. A 101 (1997) in press.

Sincerely yours,
Bernd

-----------------------------------------------------
Dr. Bernd Kallies
Institut fuer Physikalische und Theoretische Chemie
Universitaet Potsdam
Am Neuen Palais 10
14469 Potsdam
GERMANY
e-mail: [email-masked]
WWW   : http://www.chem.uni-potsdam.de/~kallies/kallies.htm
Tel   : [+49] (0)331 / 977-1313
Fax   : [+49] (0)331 / 977-1315
-----------------------------------------------------
========================================================
Elmar Gerwalin ,   University of Kaiserslautern
                   Dept. of Theoretical Chemistry
                   Erwin-Schroedinger-Str.
                   67663 Kaiserslautern, Germany

                   http://iris2.chemie.uni-kl.de
                   [email-masked]
========================================================

>From [email-masked]  Mon Jan 25 19:37:13 1999
Date: Mon, 25 Jan 1999 12:37:12 -0600
To: Didier MATHIEU <[email-masked]>
From: Ernest Chamot <[email-masked]>
Subject: Re: CCL:Hydrogen Bonds with DFT / GGA

Hi Didier,

You asked:

>I read somewhere that DFT was not very good at describing hydrogen
>bonds.
>I wonder if anybody can provide me some details about this subject, i.e.
>performance of DFT with regard to hydrogen bonds.

I use DFT a fair amount, and try to keep track of its strengths and
weaknesses.  The ability of DFT to describe hydrogen bonds (like so many
other properties) has been improved by the use of gradient corrections, so
that earlier generalizations of whether DFT is or isn't good at describing
H-bonds are no longer appropriate.

 Sim, St-Amant, Papai, & Salahub, J. Am. Chem. Soc., 114, 4391-400 (1992).

The accuracy will depend on the GGA used.  Here are some estimates (and
sources) of the accuracy of DFT calculations (including BP calculations,
since  you stated that you had been using that GGA) on H-bonded systems:

1) Earlier, bond lengths for a couple of H-bond systems were found accurate
only to within ~ 0.1 and 0.3 A respectively  with BP and VWN:

 See "Density Functional Methods in Chemistry," Labanowski & Andzelm Ed.,
Springer-Verlag (1991).

2) The B88P92 combination was supposed to be better for H-bonds:

 Perez-Jorda & Becke, Chem. Phys. Lett., 233, 134-7 (1995).

3) A comparison of BLYP & B3-LYP/ACM GGA's  with several ionic H-bonds was
reported to this list to calculate bond lengths within ~ 0.02-0.04 A and
energies within ~ 2 kcal:

 See posting to CCL by A. T. Pudzianowski, 5/3/95.

4) A related calculation, would be to compare the accuracy of proton
affinities.  These have been found to be accurate within ~ 4 kcal for BP
and VWN, and ranging from ~ 0.1 to 2 kcal for B3LYP/ACM:

 Fitzgerald & Andzelm, J. Phys. Chem., 95, 10531-4 (1991).
 Reported by A. Becke, San Francisco ACS Meeting, PHYS248, April, 1997.
 P. Redfern, J-P Blaudeau, & L. Curtiss, J. Phys. Chem. A, 101(46), 8701-5
(1997).

Finally, you mentioned that you saw a problem with an amino-nitro aromatic:

>I have carried out some calculations of energetic data for molecules
>including nitroaromatics with gradient-corrected DFT functionals,
>especially Becke-Perdew86.
>The results are satisfactory excepted for tri-amino-trinitro-benzene,
>the only molecule in my dataset showing intramolecular hydrogen bond.

Out of curiosity, when you say the results are unsatisfactory, are you
comparing against experimental data measured in the presence of a solvent?
And if so, are you including solvent effects in your calculations?
Nitroaromatics (specifically their radical anions) can show some subtle
changes in geometry that can significantly change the energies. Cramer et.
al. have reported some dramatic differences accurately reproduced with
their semiempirical solvation model calculations (SM2 etc.):

Initially in ECTOC-1, paper #46, 6/12/95;
http://www.ch.ic.ac.uk/ectoc/ectoc-1.html

And I have seen this in my own calculations using the COSMO solvation
model, which has since been implemented in combination with DFT:

 J. Andzelm, C. Kolmel, & A. Klamt, J. Chem. Phys., 103(21), 9312-20 (1995).

I hope this helps.

EC
---

Ernest Chamot
Chamot Laboratories, Inc.
530 E. Hillside Rd.
Naperville, IL 60540
(630) 637-1559
[email-masked]
http://www.chamotlabs.com/cl

>From [email-masked]  Mon Jan 25 18:07:10 1999
Date: Mon, 25 Jan 1999 18:07:10 +0100
From: Regis Gautier <[email-masked]>
To: Didier MATHIEU <[email-masked]>
Subject: Re: CCL:Hydrogen Bonds with DFT / GGA

Bonjour,

Il s'avere que le cas des liaisons faibles comme les liaisons hydrogene
n'est pas maitrise par les fonctionelles GGA comme BP86. Il apparait
que les fonctionelles hybrides conduisent a de meilleurs resultats comme
B3LYP.
Voir : H. Chermette, L'Actualite Chimique 1996, 7 ,10-15 et ref citees

Cordialement,

R. Gautier

> Hello everybody,

>
> I have carried out some calculations of energetic data for molecules
> including nitroaromatics with gradient-corrected DFT functionals,
> especially Becke-Perdew86.
> The results are satisfactory excepted for tri-amino-trinitro-benzene,
> the only molecule in my dataset showing intramolecular hydrogen bond.
> I read somewhere that DFT was not very good at describing hydrogen
> bonds.
> I wonder if anybody can provide me some details about this subject, i.e.
> performance of DFT with regard to hydrogen bonds.
>
> Thank you.
> Regards
>

-------------------------------------------------------------
 Regis GAUTIER
 Max-Planck-Institut fur Festkorperforschung
 Heisenbergstr. 1, 70569 Stuttgart, Germany
 E-mail: [email-masked]
 Tel: +49 711 689-1566 ; Fax: +49 711 689-1632
-------------------------------------------------------------

>From [email-masked]  Mon Jan 25 17:19:24 1999
Date: Mon, 25 Jan 1999 10:17:27 -0600 (CST)
From: Carlo Adamo <[email-masked]>
To: [email-masked]

Ciao Didier,

I did some works about DFT & H-bond. Please give a look at these papers:

Chem. Phys. Lett. 224 (1994) 432
Chem. Phys. Lett. 231 (1994) 295
J. Chem. Phys. 102 (1995) 364
Int. J. Quantum. Chem. 56 (1995) 697
J. Phys. Chem.  99 (1995) 15062
J. Chem. Phys. 105 (1996) 11007
Int. J. Quantum. Chem. 61 (1997) 429
J. Comp. Chem.  18 (1997) 1993

a review was published in:
Recent Advances in Density Functional Methods, Part II, Edited by
D.P. Chong, World Scientific Press, Singapore (1997).

Furthermore the computation of H-bond strength in small complexes, as 
water dimer, is one of the tests to check the performances of
new functionals. So you might find some informations also in

J. Chem. Phys. 108 (1998) 664
J. Comp. Chem.  19 (1998) 418

Carlo

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