Supporting Information for. Grafting trimethylaluminum and its halogen derivatives on silica: General trends for
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1 Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics. This journal is the Owner Societies 2015 Supporting Information for Grafting trimethylaluminum and its halogen derivatives on silica: General trends for 27 Al SS-NMR response from first principles calculations Rachel Nathaniel Kerber, # Philippe Sautet* Torsten Kerber,^ Xavier Rozanska, Δ Françoise Delbecq, and Université de Lyon, CNRS, Institut de Chimie de Lyon, Ecole Normale Supérieure de Lyon, 46 allée d Italie, F Lyon Cedex 07, France. # Present address: University of Cambridge, Department of Chemistry, Lensfield Road, Cambridge, CB2 1EW, United Kingdom. ^ Present address: think-cell Software, Chausseestr. 8E, Berlin, Germany. Δ Present address: Materials Design, 18 rue de Saisset, F Montrouge, France. *Corresponding author: Philippe.Sautet@ens-lyon.fr Contents 27 AL SS- NMR FOR MONOMERIC SPECIES IN GAS- PHASE AND GRAFTED ON SILICA AL SS- NMR FOR DIMERIC SPECIES... 4 DIMERIC SPECIES IN GAS PHASE... 4 DIMERIC SPECIES GRAFTED ON SILICA... 8 Monografted dimers... 8 Bigrafted dimers
2 27 Al SS- NMR for monomeric species in gas- phase and grafted on silica 27 Al SS- NMR for monomeric species in gas- phase and grafted on silica Monomers in gas- phase and grafted Species δ ISO (ppm) CQ (MHz) Gas- phase AlF AlCl Al(OH) Al(OH) 2 Cl Al(OH)Cl Al(OH) 2 Me Al(OH)Me Al(OH)MeCl Al(OMe) Al(Me) AlMe 2 Cl AlMeCl Cluster models Al(OSi(OH) 3 ) AlMe(OSi(OH) 3 ) AlMe 2 (OSi(OH) 3 ) AlMeCl(OSi(OH) 3 ) Surface models O SURF AlMe (O SURF ) 2 AlMe O SURF AlMeCl (O SURF ) 2 AlMeCl O SURF AlCl (O SURF ) 2 AlCl (O SURF ) 2 AlMe (O SURF ) 2 AlCl Table S1. DFT-calculated 27 Al NMR parameters δ ISO (ppm) and C Q (MHz) for all monomeric species presented in Figure 1. 2
3 Scheme S1. Schematic representation of all models of Al monomers used in the 2D map: AlMe 3, AlMe 2 Cl, AlMeCl 2, AlMe 2 OH, AlCl 2 OH, AlMe(OH) 2, AlCl(OH) 2, AlMeClOH, Al(OH) 3, Al(OMe) 3, AlF 3, Al(OSi(OH) 3 ) 3, AlMe(OSi(OH) 3 ) 2, AlMe 2 (OSi(OH) 3 ), AlMeCl(OSi(OH) 3 ), O SURF AlMe 2, O SURF AlMeCl, O SURF AlCl 2, O SURF AlMe 2 O SURF, O SURF AlMeCl O SURF, O SURF AlCl 2 O SURF, (O SURF ) 2 AlMe, (O SURF ) 2 AlCl. 3
4 27 Al SS- NMR for dimeric species Dimeric species in gas phase Figure S1 Relative energy as a function of the number of Cl for the dimers in gas phase with general formula Me n Cl 2-n Al1(µ 2 -Me n Cl 1-n )Al2Me n Cl 2-n. The small c and t, stand for cis and trans isomers, respectively. The crossed diamond represents Me in bridge position, the circle corresponds to mixed MeCl bridge, and the star shows that in bridge we have Cl. The position of the Cl atoms is indicated as in the main text of the paper. 4
5 Relative energies of gas- phase dimers Species Number of Cl atoms Cl position Me2Al1(µ 2 -Me)Al2Me Me 2 Al1(µ-MeCl)Al2Me Me 2 Al1(µ 2 -Me)Al2MeCl Me2Al1(µ 2 -Cl)Al2Me Me2Al1(µ-MeCl)Al2MeCl MeClAl1(µ 2 -Me)Al2MeCl 101t MeClAl1(µ 2 -Me)Al2MeCl 101c Me2Al1(µ 2 -Me)Al2Cl Me2Al1(µ 2 -Cl)Al2MeCl MeClAl1(µ-MeCl)Al2MeCl 111t MeClAl1(µ-MeCl)Al2MeCl 111c Me 2 Al1(µ-MeCl)Al2Cl MeClAl1(µ 2 -Me)Al2Cl MeClAl1(µ 2 -Cl)Al2MeCl 121t MeClAl1(µ 2 -Cl)Al2MeCl 121c Me 2 Al1(µ 2 -Cl)Al2Cl MeClAl1(µ-MeCl)Al2Cl Cl 2 Al1(µ 2 -Me)Al2Cl MeClAl1(µ 2 -Cl)Al2Cl Cl 2 Al1(µ-MeCl)Al2Cl Cl 2 Al1(µ 2 -Cl)Al2Cl Table S2. Relative energy differences for the bigrafted dimers in gas phase as a function of the number of Cl with general formula Me n Cl 2-n Al1-(µ 2 -Me n Cl 1-n )Al2Me n Cl 2-n. 5
6 Gas- phase dimers Species δ ISO CQ Cl positions Al (ppm) (MHz) Me 2 Al1(µ 2 -Me)Al2Me Al Al Me2Al1(µ2-Me)Al2MeCl 0 01 Al Al Me2Al1(µ2-Me)Al2Cl Al Al MeClAl1(µ2-Me)Al2MeCl c 101c Al Al MeClAl1(µ2-Me)Al2MeCl t 101 * t Al Al MeClAl1(µ2-Me)Al2Cl Al Al Cl2Al1(µ2-Me)Al2Cl2 202 Al Al Me2Al1(µ-MeCl)Al2Me2 010 Al Al Me2Al1(µ-MeCl)Al2MeCl 0 11 Al Al Me2Al1(µ-MeCl)Al2Cl Al Al MeClAl1(µ-MeCl)Al2MeCl c 111c Al Al MeClAl1(µ-MeCl)Al2MeCl t 111t Al Al MeClAl1(µ-MeCl)Al2Cl Al Al Cl2Al1(µ-MeCl)Al2Cl2 212 Al Al Me 2 Al1(µ 2 -Cl)Al2Me * Al Al Me 2 Al1(µ 2 -Cl)Al2MeCl 0 21 Al Al Me 2 Al1(µ 2 -Cl)Al2Cl Al Al MeClAl1(µ 2 -Cl)Al2MeCl c Al c Al MeClAl1(µ 2 -Cl)Al2MeCl t Al t Al MeClAl1(µ 2 -Cl)Al2Cl Al Al Cl 2 Al1(µ 2 -Cl)Al2Cl Al Al Table S3. DFT-calculated 27 Al NMR parameters δ ISO (ppm) and C Q (MHz) for all dimeric species in gas-phase presented in Figure 2. Small c and t are indicating the cis and trans position of the substituent. Labels x yz and xy z indicate the position of the considered Al 6
7 (Al1(left) and Al2(right). In bold are the two dimer references used for the EFG calculations in terms of NBOs and NLMOs. Me Me Al O O Al Me Me O Me Al Me Me Al Me O t Scheme S2. Representation of the two dimers with methyl and oxygen substituents used for the decomposition on localized molecular orbitals. NLMO contributions # 020 # 101 BD σ(al-c) BD σ(al-o) Σσ(Al-X) BD σ(c-h) C (Al 1 -Al 2 -C) Al core C core O core ΣAnalysis # Total calculated V NBO charges Al Cl C t C br Table S4 NLMO analysis of aluminum V 33 (in au) principal component for Me 2 Al1(µ 2 -OSiH 3 )Al2Me 2 and Me(OSiH 3 )Al1(µ 2 -Me)Al2Me(OSiH 3 ) dimers in gas phase. Here are presented the following labels: 2-center bond (BD), 3-center bond (3C), and 1-center core pair (CR). Total calculated is the actual V 33. ΣAnalysis corresponds to the sums of all terms shown here from NLMO analysis with >5% contribution. 7
8 Dimeric species grafted on silica Monografted dimers Relative energies of Species monografted dimers Type / Cl Number of Cl atoms position Me 2 Al1(µ-MeO SURF )Al2Me / O SURF MeAl1(µ 2 -Me)Al2Me / Me 2 Al1(µ-ClO SURF )Al2Me / Me 2 Al1(µ-MeO SURF )Al2MeCl 2.1 / O SURF MeAl1(µ-MeCl)Al2Cl / O SURF ClAl1(µ 2 -Me)Al2Cl / O SURF MeAl1(µ 2 -Me)Al2MeCl 2.2 / Me 2 Al1(µ-ClO SURF )Al2MeCl 2.1 / MeClAl1(µ-MeO SURF )Al2MeCl trans 2.1 / 101t O SURF MeAl1(µ 2 -Cl)Al2Me / Me 2 Al1(µ-MeO SURF )Al2Cl / MeClAl1(µ-MeO SURF )Al2MeCl cis 2.1 / 101c O SURF ClAl1(µ-MeCl)Al2Me / O SURF MeAl1(µ-MeCl)Al2MeCl 2.2 / O SURF ClAl1(µ 2 -Me)Al2MeCl cis 2.2 / 101c O SURF MeAl1(µ 2 -Me)Al2Cl / O SURF ClAl1(µ 2 -Me)Al2MeCl trans 2.2 / 101t MeClAl1(µ-ClO SURF )Al2MeCl trans 2.1 / 111t Me 2 Al1(µ-ClO SURF )Al2Cl / MeClAl1(µ-ClO SURF )Al2MeCl cis 2.1 / 111c O SURF ClAl1(µ 2 -Cl)Al2Me / O SURF MeAl1(µ 2 -Cl)Al2MeCl 2.2 / MeClAl1(µ-MeO SURF )Al2Cl / O SURF ClAl1(µ-MeCl)Al2MeCl cis 2.2 / 111c O SURF MeAl1(µ-MeCl)Al2Cl / O SURF ClAl1(µ-MeCl)Al2MeCl trans 2.2 / 111t O SURF ClAl1(µ 2 -Me)Al2Cl / MeClAl1(µ-ClO SURF )Al2Cl / O SURF ClAl1(µ 2 -Cl)Al2MeCl cis 2.2 / 121c O SURF MeAl1(µ2-Cl)Al2Cl / O SURF ClAl1(µ2-Cl)Al2MeCl trans 2.2 / 121t Cl 2 Al1(µ-MeO SURF )Al2Cl / O SURF ClAl1(µ-MeCl)Al2Cl / Cl 2 Al1(µ-ClO SURF )Al2Cl / O SURF ClAl1(µ 2 -Cl)Al2Cl / Table S4. Relative energy differences for the monografted dimers- grafted via terminal (GvT) and grafted via bridge (GvB) as a function of the number of Cl with general formula O SURF Me n Cl 1-n Al1-(µ 2 -Me n Cl 1-n )Al2Me n Cl 2-n and Me n Cl 2-n Al1(µ-Me n Cl 1-n O SURF )Al2Me n Cl 2-n, respectively. 8
9 GvB Species Cl δ ISO CQ Al position (ppm) (MHz) Me 2 Al1(µ-MeO SURF )Al2Me Al Al Me 2 Al1(µ-MeO SURF )Al2MeCl 001 Al Al Me 2 Al1(µ-MeO SURF )Al2Cl Al Al MeClAl1(µ-MeO SURF )Al2MeCl c 101c Al Al MeClAl1(µ-MeO SURF )Al2MeCl t 101t Al Al MeClAl1(µ-MeO SURF )Al2Cl Al Al Cl 2 Al1(µ-MeO SURF )Al2Cl Al Al Me 2 Al1(µ-ClO SURF )Al2Me Al Al Me 2 Al1(µ-ClO SURF )Al2MeCl 011 Al Al Me 2 Al1(µ-ClO SURF )Al2Cl Al Al MeClAl1(µ-ClO SURF )Al2MeCl c 111c Al Al MeClAl1(µ-ClO SURF )Al2MeCl t 111t Al Al MeClAl1(µ-ClO SURF )Al2Cl Al Al Cl 2 Al1(µ-ClO SURF )Al2Cl Al Al Table S5. DFT-calculated 27 Al NMR parameters δ ISO (ppm) and C Q (MHz) for all GvB species (Me n Cl 2-n Al1(µ-Me n Cl 1-n O SURF )Al2Me n Cl 2-n ) in Figure 5 of the manuscript. Small c and t are indicating the cis and trans position of the substituent, respectively. 9
10 Figure S2. All methylaluminum monografted dimers via terminal (GvT) position are presented in two 2D plots, one for each Al (a for Al1 and b for Al2 environments), respectively together with their chloro derivatives grafted on the {001} silica surface. 10
11 Species Cl position O SURF MeAl1(µ 2 -Me)Al2Me O SURF MeAl1(µ 2 -Me)Al2MeCl 001 O SURF ClAl1(µ 2 -Me)Al2Me O SURF MeAl1(µ 2 -Me)Al2Cl O SURF ClAl1(µ 2 -Me)Al2MeCl O SURF ClAl1(µ 2 -Me)Al2MeCl c 101t O SURF ClAl1(µ 2 -Me)Al2Cl GvT Al δ ISO CQ (ppm) (MHz) Al Al Al Al Al Al Al Al Al Al Al Al Al Al O SURF MeAl1(µ-MeCl)Al2Me Al Al O SURF MeAl1(µ-MeCl)Al2MeCl 011 Al Al O SURF ClAl1(µ-MeCl)Al2Me Al Al O SURF MeAl1(µ-MeCl)Al2Cl Al Al O SURF ClAl1(µ-MeCl)Al2MeCl 111c Al Al O SURF ClAl1(µ-MeCl)Al2MeCl 111t Al Al O SURF ClAl1(µ-MeCl)Al2Cl Al Al O SURF MeAl1(µ 2 -Cl)Al2Me O SURF MeAl1(µ 2 -Cl)Al2MeCl 021 O SURF ClAl1(µ 2 -Cl)Al2Me O SURF MeAl1(µ 2 -Cl)Al2Cl O SURF ClAl1(µ 2 -Cl)Al2MeCl O SURF ClAl1(µ 2 -Cl)Al2MeCl 121c 121t O SURF ClAl1(µ 2 -Cl)Al2Cl Al Al Al Al Al Al Al Al Al Al Al Al Al Al Table S6. DFT-calculated 27 Al NMR parameters δ ISO (ppm) and C Q (MHz) for all GvT species (O SURF Me n Cl 1-n Al1-(µ 2 -Me n Cl 1-n )Al2Me n Cl 2-n ) shown in Figure S2. Small c and t are indicating the cis and trans position of the substituent, respectively.
12 Bigrafted dimers 27 Al SS- NMR for bigrafted dimeric species on silica Relative energies of Species Type / Cl Number of Cl atoms position O SURF MeAl1(µ-MeO SURF )Al2Me 2 2.3/ Me 2 Al1(µ 2 -O SURF )Al2Me / O SURF MeAl1(µ 2 -Me)Al2MeO SURF 2.5 / (O SURF ) 2 Al1(µ 2 -Me)Al2Me / O SURF Me 2 Al1(µ-ClO SURF )Al2Me / O SURF Me 2 Al1(µ-MeO SURF )Al2MeCl 2.3 / O SURF ClAl1(µ-MeO SURF )Al2Me / O SURF MeAl1(µ-MeCl)Al2MeO SURF 2.5 / MeClAl1(µ 2 -O SURF )Al2Me / O SURF ClAl1(µ 2 -Me)Al2MeO SURF 2.5 / (O SURF ) 2 Al1(µ-MeCl)Al2Me / (O SURF ) 2 Al1(µ 2 -Me)Al2MeCl 2.6 / O SURF MeAl1(µ-ClO SURF )Al2MeCl 2.3 / O SURF ClAl1(µ-ClO SURF )Al2Me / O SURF MeAl1(µ 2 -Cl)Al2MeO SURF 2.5 / O SURF ClAl1(µ-MeO SURF )Al2MeCl 2.3 / 101t O SURF ClAl1(µ-MeO SURF )Al2MeCl 2.3 / 101c O SURF MeAl1(µ-MeO SURF )Al2Cl / (O SURF ) 2 Al1(µ 2 -Cl)Al2Me / O SURF MeAl1(µ-MeCl)Al2ClO SURF 2.5 / MeClAl1(µ 2 -O SURF )Al2MeCl 2.4 / 101c Me 2 Al1(µ 2 -O SURF )Al2Cl / (O SURF ) 2 Al1(µ-MeCl)Al2MeCl 2.6 / O SURF ClAl1(µ 2 -Me)Al2ClO SURF 2.5 / (O SURF ) 2 Al1(µ 2 -Me)Al2Cl 2.6 / O SURF ClAl1(µ-ClO SURF )Al2MeCl 2.3 / 111t O SURF ClAl1(µ-ClO SURF )Al2MeCl 2.3 / 111c O SURF MeAl1(µ-ClO SURF )Al2Cl / O SURF ClAl1(µ 2 -Cl)Al2MeO SURF 2.5 / O SURF ClAl1(µ-MeO SURF )Al2Cl / (O SURF ) 2 Al1(µ 2 -Cl)Al2MeCl 2.6 / O SURF ClAl1(µ-MeCl)Al2ClO SURF 2.5 / MeClAl1(µ 2 -O SURF )Al2Cl / (O SURF ) 2 Al1(µ-MeCl)Al2Cl / O SURF ClAl1(µ-ClO SURF )Al2Cl / O SURF ClAl1(µ 2 -Cl)Al2ClO SURF 2.5 / (O SURF ) 2 Al1(µ 2 -Cl)Al2Cl / Cl 2 Al1(µ 2 -O SURF )Al2Cl / Table S7. Relative energy differences for the bigrafted dimers- 2.3 (O SURF Me n Cl 1-n Al1(µ-Me n Cl 1- no SURF )Al2Me n Cl 2-n ), 2.4 (Me n Cl 2-n Al1(µ 2 -O SURF )Al2Me n Cl 2-n ), 2.5 (O SURF Me n Cl 1-n Al1(µ- Me n Cl 2-n )Al2Me n Cl 1-n O SURF ), and 2.6 (O SURF ) 2 Al1(µ-Me n Cl 2-n )Al2Me n Cl 2-n. 12
13 Figure S3. All methylaluminum bigrafted dimers and their chloro derivatives in which the Al-Al axis is parallel to the {001} silica surface. For the 2.4 dimers (Me n Cl 2-n Al1(µ 2 -O SURF ) Me n Cl 2-n ) we see clearly the effect of the number of the Cl atoms. Starting from Me 2 Al1(µ 2 -O SURF ) Me 2 (where Al1 and Al2 are equivalent) we start from 167 ppm and 28 MHz, to 130 ppm and 21 MHz for the MeClAl1(µ 2 -O SURF ) MeCl, and ending with 99 ppm and 15 MHz for the Cl 2 Al1(µ 2 -O SURF ) Cl 2. Along that linear correlation the δ ISO and the C Q both shift towards the small values with 68 ppm and 13 MHz respectively. This is exactly what we would expect based on the already observed trend for the monografted dimers. 13
14 Figure S4. All methylaluminum bigrafted dimers and their chloro derivatives in which the Al-Al axis is parallel to the {001} silica surface. Figure S5. All methylaluminum bigrafted dimers and their chloro derivatives in which the Al-Al axis is perpendicular to the {001} silica surface. 14
15 Species Cl position 15 Al BG dimers δ ISO (ppm) CQ (MHz) 2.3 O SURF MeAl1(µ-O SURF Me)Al2Me Al Al O SURF MeAl1(µ-O SURF Me)Al2MeCl 001 Al Al O SURF ClAl1(µ-O SURF Me)Al2Me Al Al O SURF MeAl1(µ-O SURF Me)Al2Cl Al Al O SURF ClAl1(µ-O SURF Me)Al2MeCl c 101c Al Al O SURF ClAl1(µ-O SURF Me)Al2MeCl t O SURF ClAl1(µ-O SURF Me)Al2Cl 2 101t Al Al Al Al O SURF MeAl1(µ-O SURF Cl)Al2Me Al Al O SURF MeAl1(µ-O SURF Cl)Al2MeCl 011 Al Al O SURF ClAl1(µ-O SURF Cl)Al2Me Al Al O SURF MeAl1(µ-O SURF Cl)Al2Cl Al Al O SURF ClAl1(µ-O SURF Cl)Al2MeCl c 111c Al Al t Al O SURF ClAl1(µ-O SURF Cl)Al2MeCl t Al Al O SURF ClAl1(µ-O SURF Cl)Al2Cl 2 Al Me 2 Al1(µ 2 -O SURF )Al2Me Al Al Me 2 Al1(µ 2 -O SURF )Al2MeCl 001 Al Al Me 2 Al1(µ 2 -O SURF )Al2Cl Al Al MeClAl1(µ 2 -O SURF )Al2MeCl 101 Al Al MeClAl1(µ 2 -O SURF )Al2Cl Al Al Cl 2 Al1(µ 2 -O SURF )Al2Cl Al Al O SURF MeAl1(µ 2 -Me)Al2MeO SURF 000 Al Al
16 O SURF MeAl1(µ 2 -Me)Al2ClO SURF 001 Al Al O SURF ClAl1(µ 2 -Me)Al2ClO SURF 101 Al Al O SURF MeAl1(µ-MeCl)Al2MeO SURF 010 Al Al O SURF MeAl1(µ-MeCl)Al2ClO SURF 011 Al Al O SURF ClAl1(µ-MeCl)Al2ClO SURF 111 Al Al O SURF MeAl1(µ 2 -Cl)Al2MeO SURF 020 Al Al O SURF MeAl1(µ 2 -Cl)Al2ClO SURF 021 Al Al O SURF ClAl1(µ 2 -Cl)Al2ClO SURF 121 Al Al (O SURF ) 2 Al1(µ 2 -Me)Al2Me Al Al (O SURF ) 2 Al1(µ 2 -Me)Al2MeCl 001 Al Al (O SURF ) 2 Al1(µ 2 -Me)Al2Cl Al Al (O SURF ) 2 Al1(µ-MeCl)Al2Me Al Al (O SURF ) 2 Al1(µ-MeCl)Al2MeCl 011 Al Al (O SURF ) 2 Al1(µ-MeCl)Al2Cl Al Al (O SURF ) 2 Al1(µ 2 -Cl)Al2Me Al Al (O SURF ) 2 Al1(µ 2 -Cl)Al2MeCl 021 Al Al (O SURF ) 2 Al1(µ 2 -Cl)Al2Cl Al Al Table S6. DFT-calculated 27 Al NMR parameters δ ISO (ppm) and C Q (MHz) for all bigrafted dimeric species on silica surface some of which presented in Figure 5, S2-S5.
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